Nghiên cứu tổng hợp một số dẫn xuất naphthoquinon bằng phản ứng doimino và đánh giá hoạt tính sinh học của chúng

BỘ GIÁO DỤC VÀ ĐÀO TẠO VIỆN HÀN LÂM KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ - VŨ NGỌC DOÃN NGHIÊN CỨU TỔNG HỢP MỘT SỐ DẪN XUẤT NAPHTHOQUINON BẰNG PHẢN ỨNG DOIMINO VÀ ĐÁNH GIÁ HOẠT TÍNH SINH HỌC CỦA CHÚNG LUẬN ÁN TIẾN SĨ HÓA HỌC Hà Nội - 2017 BỘ GIÁO DỤC VÀ ĐÀO TẠO VIỆN HÀN LÂM KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ - VŨ NGỌC DOÃN NGHIÊN CỨU TỔNG HỢP MỘT SỐ DẪN XUẤT NAPHTHOQUINON BẰNG PHẢN ỨNG DOIMINO VÀ ĐÁNH GIÁ HOẠT TÍNH SINH HỌC CỦA CHÚNG Chun ngành: Hóa Hữu Mã số: 62 44 01 14 LUẬN ÁN TIẾN SĨ HÓA HỌC NGƯỜI HƯỚNG DẪN KHOA HỌC GS TS Nguyễn Văn Tuyến TS Đặng Thị Tuyết Anh Hà Nội – 2017 LỜI CAM ĐOAN Tôi xin cam đoan cơng trình nghiên cứu riêng tơi cộng Các số liệu kết nêu Luận án trung thực chưa cơng bố cơng trình nghiên cứu trước Tồn thơng tin trích dẫn Luận án rõ nguồn gốc xuất xứ Hà Nội, ngày tháng năm 2017 Tác giả luận án NCS Vũ Ngọc Dỗn LỜI CẢM ƠN Với lịng biết ơn sâu sắc, em xin gửi lời cảm ơn tới tập thể thầy cô hướng dẫn khoa học GS.TS Nguyễn Văn Tuyến TS Đặng Thị Tuyết Anh Viện Hóa học, Viện Hàn lâm Khoa học Công nghệ Việt Nam giao đề tài trực tiếp định hướng, bảo giúp đỡ em tồn q trình thực Luận án Em xin chân thành cảm ơn Thầy, Cô, cán Viện Hóa học, Viện Hàn lâm Khoa học Công nghệ Việt Nam giảng dạy, hướng dẫn em hoàn thành học phần chuyên đề Chương trình đào tạo Tơi gửi lời cảm ơn chân thành đến TS Lê Nhật Thùy Giang, TS Phạm Thế Chính, KS Hồng Thị Phương, CN Nguyễn Bích Thuận cán bộ, nhân viên Phịng Hóa dược, Viện Hóa học tạo điều kiện giúp đỡ suốt thời gian thực Luận án Tôi xin gửi lời cảm ơn đến huy, lãnh đạo Bộ mơn Phịng hóa, Khoa Hóa – Lý kỹ thuật, Học viện Kỹ thuật Quân sự; Đoàn 871 Tổng cục trị, Bộ Quốc phịng; Viện Hóa học, Học viện Khoa học Công nghệ, Viện Hàn lâm Khoa học Công nghệ Việt Nam tạo điều kiện giúp đỡ thời gian, công việc, thủ tục để tơi hồn thành Luận án Cuối cùng, tơi xin gửi lời cảm ơn đến gia đình, bạn bè đồng nghiệp động viên, giúp đỡ mặt suốt trình thực Luận án Trân trọng cảm ơn! Hà Nội, ngày tháng năm 2017 Tác giả luận án NCS Vũ Ngọc Doãn DANH MỤC CÁC CHỮ CÁI VIẾT TẮT Các phương pháp sắc ký TLC Thin Layer Chromatography: Sắc ký lớp mỏng CC Column Chromatography: Sắc ký cột Các phương pháp phổ HRMS High resolution Mass Spectroscopy: Phổ khối lượng phân giải cao ESI-MS Electrospray Ionization Mass Spectroscopy: Phổ khối ion hóa phun điện IR Infrared Spectroscopy: Phổ hồng ngoại ATR Attenuated total reflection Proton Nuclear Magnetic Resonance Spectroscopy: Phổ cộng H-NMR hưởng từ hạt nhân proton 13 C-NMR Carbon-13 Nuclear Magnetic Resonance Spectroscopy: Phổ cộng hưởng từ hạt nhân carbon 13 s: singlet d: doublet m: multiplet dd: double doublet t: triplet q: quartet dt: doublet triplet Các chữ viết tắt khác IC50 The half maximal inhibitory concentration: Nồng độ tác dụng ức chế 50% tăng sinh dòng tế bào thử nghiệm KB Human epidermic carcinoma: Dịng tế bào ung thư Biểu mơ HepG2 Human Hepatocellular carcinoma: Dòng tế bào ung thư gan Lu Lung cancer: Dòng tế bào ung thư phổ MCF-7 Dòng tế bào ung thư vú MW Vi sóng ∆ Hồi lưu rt Nhiệt độ phòng DMPU 1,3-Đimetyltetrahydro-2(1H)-pyrimidinon THF Tetra hydro furan CAN Ceri(IV) amoni nitrat DIAD Điisopropyl azodicacboxylat TMS-N3 Trimetylsilyl azid TBAF Tetra-n-butylammoni florua LDA Liti điisopropyl amin MeCN Axeton nitril Et3N Trietylamin EtOH Etanol DBU 1,8-Điazabicyclo-[5.4.0]undec-7-en AcOH Axit axetic mCPBA Axit m-clopeoxitbenzoic L-Pro L-Propine DMF Đimetyl focmamit TDAE Tetrakis (đimetyl amino) etylen t-BuOH tert-Butanol i-PrOH Iso Propanol BnNH2 Benzylamin PPh3 Triphenyl phosphin MeOH Metanol EtOAc Etyl axetat (DHQ)2PH Hydroquinin 1,4-phthalazinediyl diete AL Et3SiH Trietyl silan BF3.OEt2 Bo triflo etyl ete Et2O Đietyl ete p-TsOH Axit p-Toluen sunfonic ADN Axit đeoxiribonucleic ARN Axít ribonucleic DANH MỤC CÁC BẢNG BIỂU Bảng Tên bảng Trang Bảng 2.1 Chi tiết thực nghiệm tổng hợp hợp chất 169 35 Bảng 2.2 Chi tiết thực nghiệm tổng hợp hợp chất 181 45 Bảng 2.3 Chi tiết thực nghiệm tổng hợp hợp chất 188 54 Bảng 2.4 Chi tiết thực nghiệm tổng hợp hợp chất 199 65 Bảng 3.1 Ảnh hưởng dung môi thời gian phản ứng đến hiệu suất tổng hợp hợp chất 169a 82 Bảng 3.2 Các hợp chất triflometylat tetrahydrobenzo[g]chromen 169a-l 83 Bảng 3.3 Ảnh hưởng dung môi thời gian phản ứng đến hiệu suất tổng hợp hợp chất 181a 92 Bảng 3.4 Các hợp chất 2,3-dihydronaphtho[2,3-b]furan-4,9-dion 181a-l 93 Bảng 3.5 Ảnh hưởng dung môi thời gian phản ứng đến hiệu suất tổng hợp hợp chất 188a 99 Bảng 3.6 Các hợp chất benzo[h]cinnolin-5,6-dion 188a-o 100 Bảng 3.7 Ảnh hưởng dung môi thời gian phản ứng đến hiệu suất tổng hợp hợp chất 199a 108 Bảng 3.8 Các hợp chất benzo[f]indol-4,9-dion 199a-n 109 Bảng 3.9 Kết thử hoạt tính gây độc tế bào hợp chất benzo[h]cinnolin-5,6dion tổng hợp 188a-o 116 DANH MỤC CÁC HÌNH Hình Tên hình Trang Hình 1.1 Cấu trúc axit quinic số khung quinon Hình 1.2 Một số dị vòng quan trọng naphthoquinon Hình 1.3 Tương tác naphthoquinon với hệ chuyển điện tử Hình 1.4 Tương tác naphthoquinon nhờ chế alkyl hóa khử sinh học Hình 1.5 Một số phương pháp tổng hợp dị vịng naphthoquinon Hình 1.6 Một số hợp chất pyranonaphthoquinon 10 Hình 1.7 Cấu trúc isoeleutherin dẫn xuất 11 Hình 1.8 Một số hợp chất ventiloquinon 11 Hình 1.9 Các hợp chất nanaomycin tự nhiên 14 Hình 1.10 Cấu trúc frenolicin deoxyfrenolicin 14 Hình 1.11 Cấu trúc pentalongin psychorubrin 15 Hình 1.12 Cấu trúc α-lapachon β-lapachon 18 Hình 1.13 Cấu trúc số hợp chất naphtho[2,3-b]furan tự nhiên 22 Hình 1.14 Cấu trúc kinamycin A utahmycin B 26 Hình 1.15 Một số phương pháp tổng hợp dị vịng benzo[f]indol-4,9-dion 27 Hình 3.1 Dạng tồn cân chuyển hóa chất 11 phản ứng 78 Hình 3.2 Phổ 1H-NMR chất 135 79 Hình 3.3 Phổ IR hợp chất 169b 85 Hình 3.4 Phổ 1H-NMR hợp chất 169b 86 Hình 3.5 Phổ giãn 1H-NMR hợp chất 169b 86 Hình 3.6 Phổ 13C-NMR hợp chất 169b 87 Hình 3.7 Phổ giãn 13C-NMR hợp chất 169b 88 Hình 3.8 Phổ ESI-MS [M-H]- hợp chất 169b 88 Hình 3.9 Phổ ESI-MS [M+H]+ hợp chất 169b 89 C.33.44.55.54.78.65.5.43.22.2.4 22.Tai lieu Luan 66.55.77.99 van Luan an.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.33.44.55.54.78.655.43.22.2.4.55.22 Do an.Tai lieu Luan van Luan an Do an.Tai lieu Luan van Luan an Do an Hình 3.10 Cấu trúc tinh thể hợp chất 169b 89 Hình 3.11 Phổ IR hợp chất 181b 94 Hình 3.12 Phổ 1H-NMR hợp chất 181b 94 Hình 3.13 Phổ giãn 1H-NMR hợp chất 181b 95 Hình 3.14 Phổ 13C-NMR hợp chất 181b 96 Hình 3.15 Phổ giãn 13C-NMR hợp chất 181b 96 Hình 3.16 Cấu trúc tinh thể hợp chất 181b 97 Hình 3.17 Phổ IR hợp chất 188f 101 Hình 3.18 Phổ 1H-NMR hợp chất 188f 103 Hình 3.19 Phổ giãn 1H-NMR hợp chất 188f 103 Hình 3.20 Phổ 13C-NMR hợp chất 188f 104 Hình 3.21 Phổ giãn 13C-NMR hợp chất 188f 104 Hình 3.22 Cấu trúc tinh thể hợp chất 188f 105 Hình 3.23 Phổ IR hợp chất 199k 110 Hình 3.24 Phổ 1H-NMR hợp chất 199k 111 Hình 3.25 Phổ giãn 1H-NMR hợp chất 199k 111 Hình 3.26 Phổ 13C-NMR hợp chất 199k 112 Hình 3.27 Phổ giãn 13C-NMR hợp chất 199k 113 Hình 3.28 Phổ HRMS-ESI hợp chất 199k 113 Hình 3.29 Cấu trúc tinh thể hợp chất 199k 114 Hình 3.30 Cấu trúc phân tử hoạt tính gây độc tế bào hợp chất 188 118 Stt.010.Mssv.BKD002ac.email.ninhd 77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77t@edu.gmail.com.vn.bkc19134.hmu.edu.vn.Stt.010.Mssv.BKD002ac.email.ninhddtt@edu.gmail.com.vn.bkc19134.hmu.edu.vn C.33.44.55.54.78.65.5.43.22.2.4 22.Tai lieu Luan 66.55.77.99 van Luan an.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.33.44.55.54.78.655.43.22.2.4.55.22 Do an.Tai lieu Luan van Luan an Do an.Tai lieu Luan van Luan an Do an 127 properties European journal of medicinal chemistry, 2016, 110, 280-290 [28] Ryu, C.-K.; Choi, I H.; Lee, J Y.; SEONG, H J., Synthesis of benzo [b] naphtho [2, 3-d] thiophene-6, 11-diones via palladium (II) acetate-mediated cyclization of 3-arylthio-1,4-naphthoquinone Heterocycles, 2005, 65, 1205-1214 [29] Tapia, R A.; Alegria, L.; Pessoa, C D.; Salas, C.; Cortés, M J.; Valderrama, J A.; Sarciron, M.-E.; Pautet, F.; Walchshofer, N.; Fillion, H., Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring Bioorganic & medicinal chemistry, 2003, 11, 2175-2182 [30] Valderrama, J A.; Astudillo, C.; Tapia, R A.; Prina, E.; Estrabaud, E.; Mahieux, R.; Fournet, A., Studies on Quinones Part 37 Synthesis and Biological Activity of o-Aminoester Functionalised Benzo-and Naphtho[2, 3-b]thiophenequinones Chemical and pharmaceutical bulletin, 2002, 50, 1215-1218 [31] Valderrama, J A.; Espinoza, O.; Rodriguez, J.; Theoduloz, C., Synthesis and Antitumor Evaluation of Thiophene Analogs of Kigelinone Letters in Organic Chemistry, 2009, 6, 278-281 [32] Hamdan, A J.; Al-Jaroudi, S., Reactions of 2-amino-1,4-naphthoquinone with aldehydes Arabian Journal for Science and Engineering, 2003, 28, 51-60 [33] Luu, Q H.; Mito, S., Preparation of indolequinones and their applications in organic synthesis Tetrahedron, 2015, 71, 895-916 [34] Lee, J H.; Cheong, J.; Park, Y M.; Choi, Y H., Down-regulation of cyclooxygenase-2 and telomerase activity by β-lapachone in human prostate carcinoma cells Pharmacological research, 2005, 51, 553-560 [35] Skibo, E B.; Xing, C.; Dorr, R T., Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: structure-activity relationships for cytotoxicity and antitumor activity Journal of medicinal chemistry, 2001, 44, 3545-3562 [36] Gafner, S.; Wolfender, J.-L.; Nianga, M.; Stoeckli-Evans, H.; Hostettmann, K., Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots Phytochemistry, 1996, 42, 1315-1320 Stt.010.Mssv.BKD002ac.email.ninhd 77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77t@edu.gmail.com.vn.bkc19134.hmu.edu.vn.Stt.010.Mssv.BKD002ac.email.ninhddtt@edu.gmail.com.vn.bkc19134.hmu.edu.vn C.33.44.55.54.78.65.5.43.22.2.4 22.Tai lieu Luan 66.55.77.99 van Luan an.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.33.44.55.54.78.655.43.22.2.4.55.22 Do an.Tai lieu Luan van Luan an Do an.Tai lieu Luan van Luan an Do an 128 [37] Tabata, M.; Tsukada, M.; Fukui, H., Antimicrobial activity of quinone derivatives from Echium lycopsis callus cultures Planta medica, 1982, 44, 234-236 [38] dos Santos, A F.; Ferraz, P A.; de Abreu, F C.; Chiari, É.; Goulart, M O.; SantAna, A E G., Molluscicidal and trypanocidal activities of 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Benzo[g]isoquinoline-5,10-dione Derivatives as DNA Intercalators Tetrahedron, 2000, 56, 5147-5155 [44] Shchekotikhin, A E.; Glazunova, V A.; Dezhenkova, L G.; Shevtsova, E K.; Traven, V F.; Balzarini, J.; Huang, H.-S.; Shtil, A A.; Preobrazhenskaya, M N., The first series of 4, 11-bis [(2-aminoethyl) amino]anthra[2,3-b]furan-5,10-diones: Synthesis and anti-proliferative characteristics European journal of medicinal chemistry, 2011, 46, 423-428 [45] Tang, H.; Wang, X.-D.; Wei, Y.-B.; Huang, S.-L.; Huang, Z.-S.; Tan, J.-H.; An, L.-K.; Wu, J.-Y.; Chan, A S.-C.; Gu, L.-Q., Oxoisoaporphine alkaloid derivatives: synthesis, DNA binding affinity and cytotoxicity European journal of medicinal chemistry, 2008, 43, 973-980 [46] Moore, H W.; Czerniak, R., Naturally occurring quinones as potential Stt.010.Mssv.BKD002ac.email.ninhd 77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77t@edu.gmail.com.vn.bkc19134.hmu.edu.vn.Stt.010.Mssv.BKD002ac.email.ninhddtt@edu.gmail.com.vn.bkc19134.hmu.edu.vn C.33.44.55.54.78.65.5.43.22.2.4 22.Tai lieu Luan 66.55.77.99 van Luan an.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.33.44.55.54.78.655.43.22.2.4.55.22 Do an.Tai lieu Luan van Luan an Do an.Tai lieu Luan van Luan an Do an 129 bioreductive alkylating agents Medicinal research reviews, 1981, 1, 249-280 [47] Kramer, C S.; Nieger, M.; Bräse, S., Naphthoquinone Diels–Alder Reactions: Approaches to the ABC Ring System of Beticolin European Journal of Organic Chemistry, 2014, 2014, 2150-2159 [48] Claessens, S.; Verniest, G.; 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77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77t@edu.gmail.com.vn.bkc19134.hmu.edu.vn.Stt.010.Mssv.BKD002ac.email.ninhddtt@edu.gmail.com.vn.bkc19134.hmu.edu.vn C.33.44.55.54.78.65.5.43.22.2.4 22.Tai lieu Luan 66.55.77.99 van Luan an.77.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.37.99.44.45.67.22.55.77.C.33.44.55.54.78.655.43.22.2.4.55.22 Do an.Tai lieu Luan van Luan an Do an.Tai lieu Luan van Luan an Do an 131 Studies Synthetic Communications, 2016 [65] Bianchi, C.; Ceriotti, G., Chemical and pharmacological investigations of constituents of Eleutherine bulbosa (Miller) Urb.(Iridaceae) Journal of pharmaceutical sciences, 1975, 64, 1305-1308 [66] Dreyer, D L.; Arai, I.; Bachman, C D.; Anderson Jr, W R.; 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