Khóa luận tốt nghiệp: Tổng hợp một số dẫn xuất mới chứa dị vòng thiazolidine từ hợp chất 2mercapto3phenylquinazolin4(3H)one

Mục tiêu nghiên cứu của đề tài là tổng hợp một số dẫn xuất của N(5aryliden4oxo2thioxothiazolidin3yl) 2((4oxo3phenyl3,4dihydroquinazolin2yl)thio)acetamide) từ acid anthranilic và phenylisothiocyanate; nghiên cứu cấu trúc của các hợp chất đã tổng hợp bằng các phương pháp vật lí hiện đạại như phổ hồng ngoại, phổ cộng hưởng từ hạt nhân, phổ khối... Đề tài Hoàn thiện công tác quản trị nhân sự tại Công ty TNHH Mộc Khải Tuyên được nghiên cứu nhằm giúp công ty TNHH Mộc Khải Tuyên làm rõ được thực trạng công tác quản trị nhân sự trong công ty như thế nào từ đó đề ra các giải pháp giúp công ty hoàn thiện công tác quản trị nhân sự tốt hơn trong thời gian tới.

BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM TP.HCM KHOA HÓA HỌC KHÓA LUẬN TỐT NGHIỆP TỔNG HỢP MỘT SỐ HỢP CHẤT MỚI CHỨA DỊ VÒNG THIAZOLIDINE TỪ 2-MERCAPTO-3PHENYLQUINAZOLIN-4(3H)-ONE Chuyên ngành: HÓA HỮU CƠ 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b Cán hướng dẫn: PGS.TS NGUYỄN TIẾN CÔNG Sinh viên thực hiện: ĐÀO HUỲNH PHÚC 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 Thành phố Hồ Chí Minh, tháng năm 2019 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 TRƯỜNG ĐẠI HỌC SƯ PHẠM TP.HCM KHOA HÓA HỌC KHÓA LUẬN TỐT NGHIỆP TỔNG HỢP MỘT SỐ DẪN XUẤT MỚI CHỨA DỊ VÒNG THIAZOLIDINE TỪ HỢP CHẤT 2-MERCAPTO-3PHENYLQUINAZOLIN-4(3H)-ONE Chuyên ngành: HÓA HỮU CƠ XÁC NHẬN CỦA CÁN BỘ HƯỚNG DẪN (Ký tên ghi rõ họ tên) 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 PGS.TS Nguyễn Tiến Công 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f TP HCM, tháng năm 2019 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 LỜI CẢM ƠN Em xin bày tỏ lòng biết ơn sâu sắc gửi lời cảm ơn chân thành đến Thầy – PGS.TS Nguyễn Tiến Công, người quan tâm theo sát, giúp đỡ, hướng dẫn tận tình suốt q trình để em hồn thành khóa luận tốt nghiệp cách tốt Xin gửi lời cảm ơn đến thầy cô bạn động viên, giúp đỡ, tạo điều kiện tốt suốt thời gian em thực khóa luận tốt nghiệp Phịng Tổng hợp Hữu cơ, Khoa Hố học, Trường Đại học Sư phạm Thành phố Hồ Chí Minh Em xin gửi lời biết ơn đến quý Thầy, Cô giảng viên Khoa Hoá học, Trường Đại học Sư phạm Thành phố Hồ Chí Minh, người truyền đạt kiến thức khoa học quý báu học hữu ích cho em Cảm ơn bạn Nguyễn Lê Thuận tất bạn sinh viên khóa 41, Khoa Hoá học, Trường Đại học Sư phạm Thành phố Hồ Chí Minh ln gắn bó, chia sẻ, hỗ trợ tơi suốt thời gian thực khóa luận Cuối cùng, xin gửi lời cảm ơn sâu sắc đến gia đình, người ln ln tin tưởng hoàn cảnh Chân thành cảm ơn! TP Hồ Chí Minh, tháng năm 2019 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 Sinh viên thực đề tài 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 Đào Huỳnh Phúc 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 i b48182 8e6b398 c7a71a 5ee1 f02 MỤC LỤC LỜI CẢM ƠN i MỤC LỤC ii DANH MỤC CÁC BẢNG v DANH MỤC CÁC HÌNH vi DANH MỤC CÁC TỪ VIẾT TẮT vii LỜI MỞ ĐẦU CHƯƠNG TỔNG QUAN 1.1 Giới thiệu hợp chất 2-mercapto-3-phenylquinazolin-4(3H)-one phương pháp tổng hợp 1.2 Một số phản ứng chuyển hóa dị vòng 2-mercapto-3-arylquinazolin-4(3H)one 1.3 Giới thiệu dị vòng 2-thioxo-1,3-thiazolidin-4-one 15 1.4 Phương pháp tổng hợp dị vòng 2-thioxo-1,3-thiazolidin-4-one 16 1.5 Một số phản ứng chuyển hóa dị 2-thioxo-1,3-thiazolidin-4-one 17 CHƯƠNG THỰC NGHIỆM 22 2.1 Sơ đồ tổng hợp 22 2.2 Tổng hợp chất 22 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 2.2.1 Tổng hợp 2-mercapto-3-phenylquinazolin-4(3H)-one (Q) 22 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 2.2.2 Tổng hợp ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinolin-2-yl)thio)acetate 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 (QE) 23 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e 2.2.3 Tổng hợp 2-((4-oxo-3-phenyl-3,4-dihydroquinolin-2-yl)thio)acetohydrazide d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 (QH) 24 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 2.2.4 Tổng hợp N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4- 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 dihydroquinazolin-2-yl)thio)acetamide (QT) 24 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 2.2.5 Tổng hợp hợp chất N-(5-aryliden-4-oxo-2-thioxothiazolidin-3-yl)-2-((4- 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide) (QT-4OH, QT- b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 4Cl, QT-2O QT-3N) 25 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 ii b48182 8e6b398 c7a71a 5ee1 f02 2.3 Xác định tính chất số tính chất vật lý 26 2.3.1 Xác định nhiệt độ nóng chảy 26 2.3.2 Phổ hồng ngoại (IR) 26 2.3.3 Phổ cộng hưởng từ hạt nhân (NMR) 26 2.3.4 Phổ khối lượng (HR-MS) 26 CHƯƠNG 3: KẾT QUẢ VÀ THẢO LUẬN 27 3.1 Tổng hợp 2-mercapto-3-phenylquinazolin-4(3H)-one (Q) 27 3.1.1 Cơ chế phản ứng 27 3.1.2 Nghiên cứu cấu trúc 28 3.1.2.1 Phổ hồng ngoại 28 3.1.2.2 Phổ 1H-NMR 29 3.2 Tổng hợp ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (QE) 29 3.2.1 Cơ chế phản ứng 30 3.2.2 Nghiên cứu cấu trúc 31 3.2.2.1 Phổ hồng ngoại 31 3.2.2.2 Phổ 1H-NMR 32 3.3 Tổng hợp 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio) 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 acetohydrazide (QH) 33 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 3.3.1 Cơ chế phản ứng 33 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 3.3.2 Nghiên cứu cấu trúc 34 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 3.3.2.1 Phổ hồng ngoại 34 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 3.3.2.2 Phổ H-NMR 35 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 3.4 Tổng hợp N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe dihydroquinazolin-2-yl)thio)acetamide (QT) 36 f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 3.4.1 Cơ chế phản ứng 36 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 3.4.2 Nghiên cứu cấu trúc 37 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e 3.4.2.1 Phổ hồng ngoại 37 3.4.2.2 Phổ 1H-NMR 38 b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 3.4.2.3 Phổ HR-MS 39 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 iii b48182 8e6b398 c7a71a 5ee1 f02 3.5 Tổng hợp hợp chất N-(5-aryliden-4-oxo-2-thioxothiazolidin-3-yl)-2-((4oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide) (QT-2O, QT-3N, QT-4OH QT-4Cl) 40 3.5.1 Cơ chế phản ứng 40 3.5.2 Nghiên cứu cấu trúc hợp chất QT-3N, QT-2O, QT-4OH, QT-4Cl thông qua phổ hồng ngoại FT-IR 40 3.5.3 Nghiên cứu cấu trúc hợp chất QT-3N, QT-2O, QT-4OH, QT-4Cl thông qua phổ hồng ngoại 1H-NMR 42 3.5.4 Nghiên cứu cấu trúc hợp chất QT-3N, QT-2O, QT-4OH, QT-4Cl thông qua phổ 13C-NMR 45 3.5.5 Nghiên cứu cấu trúc hợp chất QT-3N, QT-2O, QT-4OH, QT-4Cl thông qua phổ HR-MS 47 CHƯƠNG 4: KẾT LUẬN 50 TÀI LIỆU THAM KHẢO 51 PHỤ LỤC 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 iv b48182 8e6b398 c7a71a 5ee1 f02 DANH MỤC CÁC BẢNG Bảng 1.1: Danh sách tác giả cơng bố nhóm vòng Bảng 1.2: Hoạt tính sinh học số hợp chất kiểm nghiệm Bảng 1.3: Hoạt tính kháng khuẩn số hợp chất kiểm nghiệm 12 Bảng 1.4: Hoạt tính kháng khuẩn số hợp chất kiểm nghiệm 15 Bảng 2.1: Kết tổng hợp số tính chất vật lý dẫn xuất N-(5-aryliden-4oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2yl)thio)acetamide) 26 Bảng 3.1: Các tín hiệu phổ FT-IR QT-2O, QT-4Cl, QT-3N QT-4OH 42 Bảng 3.2: Các tín hiệu phổ 1H-NMR QT-2O, QT-4Cl, QT-3N QT-4OH 44 Bảng 3.3: Các tín hiệu phổ 13C-NMR QT-2O, QT-4Cl, QT-3N QT-4OH 46 Bảng 3.4: Các tín hiệu phổ HR-MS QT-2O, QT-4Cl, QT-3N QT-4OH 48 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 v b48182 8e6b398 c7a71a 5ee1 f02 DANH MỤC CÁC HÌNH Hình 3.1: Phổ FT-IR hợp chất Q 28 Hình 3.2: Phổ 1H-NMR hợp chất Q 29 Hình 3.3: Phổ FT-IR hợp chất QE 31 Hình 3.4: Phổ 1H-NMR hợp chất QE 32 Hình 3.5: Phổ FT-IR hợp chất QH 34 Hình 3.6: Phổ 1H-NMR hợp chất QH 35 Hình 3.7: Phổ FT-IR hợp chất QT 37 Hình 3.8: Phổ 1H-NMR hợp chất QT 38 Hình 3.9: Phổ HR-MS hợp chất QT 39 Hình 3.10: Phổ FT-IR hợp chất QT-4Cl 41 Hình 3.11: Phổ 1H-NMR hợp chất QT-4Cl 43 Hình 3.12: Phổ 13C-NMR hợp chất QT-2O 45 Hình 3.13: Phổ HR-MS hợp chất QT-3N 47 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 vi b48182 8e6b398 c7a71a 5ee1 f02 DANH MỤC CÁC TỪ VIẾT TẮT 13 C–NMR: phổ cộng hưởng từ carbon–13 H–NMR: phổ cộng hưởng từ proton FT-IR: phổ hồng ngoại HR-MS: phổ khối lượng phân giải cao DMSO: dimethyl sulfoxide Py: pyridine DMF: Dimethyl formamide 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 vii b48182 8e6b398 c7a71a 5ee1 f02 LỜI MỞ ĐẦU Trong năm gần đây, với phát triển mạnh mẽ khoa học kỹ thuật, ngành hố học nói chung tổng hợp hữu nói riêng tạo điều kiện để phát triển Với hỗ trợ thiết bị đại, hợp chất hữu mới, mang nhiều hoạt tính sinh học mạnh không ngừng tạo với hiệu suất cao nhánh ngành tổng hợp hữu việc tổng hợp hợp chất chứa dị vòng Nhiều kết nghiên cứu cho thấy dị vịng quinazoline có số hoạt tính sinh học như: chống ung thư, chống sốt rét, chống co giật, …[1-3] Bên cạnh đó, dị vịng thiazolidine đặc biệt dẫn xuất 2-thioxo-1,3-thiazolidin-4-one có hoạt tính trội như: chống loại ung thư, virus loại vi khuẩn [18-22] Với mong muốn tìm chất thừa hưởng hoạt tính sinh học quý báu hai dị vịng quinazoline thiazolidine Chúng tơi thực đề tài: TỔNG HỢP MỘT SỐ DẪN XUẤT MỚI CHỨA DỊ VÒNG THIAZOLIDINE TỪ HỢP CHẤT 2-MERCAPTO-3-PHENYLQUINAZOLIN4(3H)-ONE 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 Nhiệm vụ đề tài: 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 ➢ Tổng hợp số dẫn xuất N-(5-aryliden-4-oxo-2-thioxothiazolidin-3-yl)- df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide) từ acid anthranilic 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e phenylisothiocyanate d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 ➢ Nghiên cứu cấu trúc hợp chất tổng hợp bằng phương pháp vật 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 lí đại phổ hồng ngoại, phổ cộng hưởng từ hạt nhân, phổ khối lượng 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 CHƯƠNG 4: KẾT LUẬN Thông qua việc thực đề tài Tổng hợp số hợp chất chứa dị vòng thiazolidine từ 2-mercapto-3-phenylquinazolin-4(3H)-one, chúng tơi tổng hợp hợp chất có chứa dị vịng quinazoline; có 05 hợp chất chứa đồng thời dị vòng quinazoline dị vòng thiazolidine (QT, QT-2O, QT-3N, QT-4Cl QT-4OH), cụ thể sau: 1) 2-mercapto-3-phenylquinazolin-4(3H)-one (Q) 2) ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (QE) 3) 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio) acetohydrazide (QH) 4) N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4 dihydroquinazolin-2-yl)thio)acetamide (QT) 5) N-(5-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)2-((4-oxo-3-phenyl-3,4-dihydroquianazolin-2-yl)thio)acetamide (QT-2O) 6) N-(5-(3-nitrobenzyllidene)-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3phenyl-3,4-dihydroquianazolin-2-yl)thio)acetamide (QT-3N) 7) N-(5-(4-chlorobenzyllidene)-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3phenyl-3,4-dihydroquianazolin-2-yl)thio)acetamide (QT-4Cl) 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 8) N-(5-(4-hydroxybenzyllidene)-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3- bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e phenyl-3,4-dihydroquianazolin-2-yl)thio)acetamide (QT-4OH) 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b Tất chất tổng hợp xác định tính chất vật lí (nhiệt độ nóng 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e chảy, trạng thái, màu sắc, tính tan, dung mơi kết tinh….) d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 Cấu trúc chất xác nhận qua phổ FT-IR, H–NMR, 13 C- NMR, HR–MS Trong 05 chất (QT, QT-2O, QT-3N, QT-4Cl QT-4OH) chưa d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c tìm thấy tài liệu mà tham khảo, 03 hợp chất (Q, QE, QH) có tính chất vật lí phù hợp với tài liệu cơng bố 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 50 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 TÀI LIỆU THAM KHẢO [1] N M A Gawad, H H Georgey, R M Youssef et al, “Design, synthesis, and anticonvulsant activity of novel quinazolinone analogues,” Medicinal Chemistry Research, vol 20, pp 1290-1286, 2011 [2] M Hagar, S M Soliman, F Ibid et al, “Synthesis, molecular structure and spectroscopic studies of some new quinazolin-4(3H)-one derivatives; an account on the N- versus S-Alkylation,” Journal of Molecular Structure, vol 1108, pp 667-679, 2016 [3] E K Ismail, I A I Ali, W Fathall et al, “Synthesis of methyl [3-alkyl-2-(2,4dioxo-3,4-dihydro-2H-quinazolin-1-yl)- acetamido] alkanoate,” The Free Internet Journal for Organic Chemistry, vol 4, pp 104-120, 2017 [4] V A and P Parthiban, “Design and Synthesis of Novel 3-(Phenyl)-2-(3-substituted propylthio) Quinazolin-4-(3H)-ones as a New Class of H1-Antihistaminic Agents,” Journal of Heterocyclic Chemistry, vol 51, pp 1615-1620, 2014 [5] D R Godani, A A Jogel, A M Sanghani et al, “New scaff of 4-oxo- thiazolidine 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 derivatives as potent anti-infective agents,” Indian Journal of Chemistry, vol 55, 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e pp 734-746, 2016 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 [6] M Saeedi, M M Khanaposhtani, P Pourrabia et al, “Design and synthesis of novel 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e quinazolinone-1,2,3-triazole hybrids as new antidiabetic agents: in vitro α - d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 glucosidase inhibition, kinetic, and docking study,” Bioorganic Chemistry, vol 83, 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 pp 1937-2016, 2018 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 [8] A M Alafeefy, “Some new quinazolin-4(3H)-one derivatives, synthesis and ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 antitumor activity,” Journal of Saudi Chemical Society, vol 15, pp 337-343, 2011 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 51 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 [9] S M H Al-Majidi and M G A A Khuzaie, “Synthesis and Antimicrobial Activity of Some New S-Substituted Quinazolinones Containing Different Heterocyclic Rings,” Asian Journal Chemistry, vol 27, pp 756-762, 2015 [10] S J Lfta, N B Ayram and S M Baqer, “Synthesis and Characterization of New2,3-Disubstituted Quinazolinone Derivatives as Antibacterial Agents,” Journal of Al-Nahrain University, vol 19, pp 1-12, 2016 [11] Z Haghighijoo, O Firuzi, B Hemmateenejad et al, “Synthesis and biological evaluation of quinazolinone-based hydrazones with potential use in Alzheimer’s disease,” Bioorganic Chemistry, vol 74, pp 126-133, 2017 [12] A A Khalil, S G A Hamide, A M Al-Obaid, “Substituted Quinazolines et al Synthesis and In-Vitro Anticancer Evaluation of New 2-Substituted Mercapto-3Hquinazoline Analogs,” Archiv der Pharmazie Pharmaceutical and Medicinal Chemistry, vol 2, pp 95-103, 2003 [13] M R Mahmoud, W S I Abou-Elmagd, S S Abdelwahab, “Synthesis and Spectral Characterization of Novel 2, 3-Disubstituted Quinazolin-4(3H) one 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 Derivatives,” American Journal of Organic Chemistry, vol 2, pp 1-8, 2012 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 [14] A A Kadi, A S El-Azab, A M Alafeefy et al, “Synthesis And Biological df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d Screening of Some New Substituted 2-Mercapto-4-(3H)-Quinazolinone Analogs 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 As Anticonvulsant Agents,” Journal of Pharmaceutical Sciences, vol 34, pp 135- 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 155, 2009 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b [15] M G A Al-Khuzaie, S M H Al-Majidi, “Synthesis, Characterization and 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c Evaluation Antimicrobial Activity of Some New substituted 2-Mercapto-3- 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e Phenyl-4(3H)-Quinazolinone,” Iraqi Journal of Science, vol 55, pp 582-593, 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 2014 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 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1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 54 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 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5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 Phụ lục 2: Phổ FT-IR hợp chất QT-4OH ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 55 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Phụ lục 3: Phổ FT-IR hợp chất QT-2O 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 56 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 Phổ dãn rộng df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 Phụ lục 4: Phổ 1H-NMR hợp chất QT-4OH d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 57 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Phổ dãn rộng 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 Phụ lục 5: Phổ 1H-NMR hợp chất QT-3N d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 58 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 Phổ dãn rộng bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 59 Phụ lục 6: Phổ H-NMR hợp chất QT-2O 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 Phổ dãn rộng 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f Phụ lục 7: Phổ 13C-NMR hợp chất QT-3N 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b Phổ dãn rộng 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 13 Phụ lục 8: Phổ C-NMR hợp chất QT-4OH ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 61 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 Phổ dãn rộng 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 Phụ lục 9: Phổ 13C-NMR hợp chất QT-4Cl df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 62 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Phụ lục 10: Phổ HR-MS hợp chất QT-4Cl 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 Phụ lục 11: Phổ HR-MS hợp chất QT-4OH 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 63 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Phụ lục 12: Phổ HR-MS hợp chất QT-2O 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 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