Luận án tiến sĩ hóa học nghiên cứu tổng hợp, xác định cấu trúc và thăm dò hoạt tính sinh học của một số phức chất pt(ii), pd(ii) với phối tử bazơ schiff

LỜI CAM ĐOAN Các kết trình bày luận án cơng trình nghiên cứu riêng tơi Các số liệu kết luận án trung thực chưa cơng bố cơng trình khác Tồn thơng tin trích dẫn luận án rõ nguồn gốc xuất xứ Tôi xin chịu trách nhiệm với lời cam đoan Hà Nội, ngày 12 tháng 12 năm 2017 Tác giả luận án NCS Lâm Quang Hải b LỜI CẢM ƠN Luận án hoàn thành Viện Hóa học - Viện Hàn lâm Khoa học & Cơng nghệ Việt Nam Tơi xin bày tỏ lịng biết ơn sâu sắc, cảm phục, kính trọng đến thầy hướng dẫn khoa học GS.TS Nguyễn Văn Tuyến, TS Nguyễn Quang Trung, người thầy tận tâm hướng dẫn khoa học, động viên, khích lệ, đạo, tạo điều kiện thuận lợi cho suốt thời gian thực hiện, hoàn thành luận án thủ tục để bảo vệ luận án Tôi xin chân thành cảm ơn đến: - GS.TS Nguyễn Văn Tuyến–Viện trưởng, GS.TSKH Trần Văn Sung Tổng biên tập tạp chí Hóa học, ThS Đặng Vũ Lương, Hội đồng Khoa học, Phịng Quản lý Tổng hợp, Phịng Hóa dược, Phịng Tổng hợp Hữu cơ, Trung tâm phân tích phổ thầy giáo, nhà khoa học Viện Hóa học giúp đỡ tơi thực hồn thành luận án; - Ban lãnh đạo, Phòng Đào tạo Nghiên cứu Khoa học Học viện Khoa học Công nghệ, đào tạo, tạo điều kiện thuận lợi giúp đỡ tơi hồn thành thủ tục suốt thời gian bảo vệ luận án cấp; - Tôi xin cám ơn đến 50 thầy/cô giáo, nhà khoa học trường Đại học, Viện nghiên cứu nước đọc viết nhận xét tóm tắt luận án gửi Học Viện; - Th.S Nghiêm Thùy Lan – Chủ tịch Cơng đồn Tập đồn Dầu khí QG Việt Nam định hỗ trợ tơi phần nhỏ kinh phí; - TS Từ Thành Nghĩa–Tổng giám đốc, TSKH Lâm Quang Chiến–Nguyên Phó Tổng giám đốc, ơng Lê Quang Mẫn–Trưởng phịng Nhân sự, Xí nghiệp Liên doanh Việt Nga–Vietsovpetro; ông Trần Văn Thường–Giám đốc, ông Nguyễn Trọng Dương–Trưởng phịng Nhân sự, Xí nghiệp Khai thác Dầu khí – OPGE; Trong q trình nghiên cứu Hà Nội, nhận nhiều động viên, giúp đỡ quý báu thầy cô, nhà khoa học anh chị Nghiên cứu sinh, bạn bè gần xa gia đình Luận án q tinh thần, tơi xin kính dâng đến cha mẹ già, gia đình bé nhỏ với tất lòng biết ơn, yêu thương trân trọng Hà Nội, ngày 12 tháng 12 năm 2017 Tác giả luận án NCS LÂM QUANG HẢI c MỤC LỤC LỜI CAM ĐOAN - b DANH MỤC CÁC KÝ HIỆU, CHỮ VIẾT TẮT - f DANH MỤC BẢNG k DANH MỤC SƠ ĐỒ - m DANH MỤC HÌNH - n MỞ ĐẦU - CHƯƠNG TỔNG QUAN - 1.1 Phối tử hữu bazơ Schiff, phức chất kim loại M(II) ứng dụng - 1.2 Nghiên cứu tổng hợp, cấu trúc hoạt tính sinh học phức chất kim loại M(II) với phối tử bazơ Schiff dạng N2O2 1.3 Nghiên cứu tổng hợp, cấu trúc hoạt tính sinh học phức chất M(II) với phối tử bazơ Schiff dạng NO 11 1.4 Tổng quan phức chất Pt(II) ứng dụng điều trị bệnh ung thư - 21 1.5 Tổng quan nghiên cứu phức chất Việt Nam 23 CHƯƠNG THỰC NGHIỆM 26 2.1 Các phương pháp nghiên cứu - 26 2.1.1 Phương pháp tổng hợp tinh chế sản phẩm 26 2.1.2 Phương pháp xác định cấu trúc 26 2.1.3 Phương pháp thử hoạt tính sinh học - 26 2.2 Kỹ thuật thực nghiệm 29 2.3 Tổng hợp salicylaldehyde có nhóm R3, R5 (phản ứng Reimer– Tiemann) 30 2.4 Tổng hợp phối tử bazơ Schiff phối tử 33 2.4.1 Tổng hợp dãy phối tử H2L1, H2L2, H2L3 33 2.4.2 Tổng hợp dãy phối tử HL4 39 2.5 Tổng hợp phức chất Pt(II) Pd(II) với phối tử bazơ Schiff 45 2.5.1 Tổng hợp phức chất với dãy phối tử H2L1, H2L2, H2L3 - 46 2.5.2 Tổng hợp phức chất với dãy phối tử HL4 56 CHƯƠNG KẾT QUẢ VÀ THẢO LUẬN 65 3.1 Nghiên cứu tổng hợp salicylaldehyde, phối tử phức chất 65 3.1.1 Nghiên cứu tổng hợp salicylaldehyde có nhóm R3, R5 65 d 3.1.2 Nghiên cứu tổng hợp phối tử phối tử - 65 3.1.3 Nghiên cứu tổng hợp phức chất với phối tử phối tử - 66 3.2 Nghiên cứu cấu trúc phối tử phức chất phương pháp phổ hồng ngoại 68 3.2.1 Phổ hồng ngoại dãy phối tử phức chất 68 3.2.2 Phổ hồng ngoại dãy phối tử phức chất 70 3.3 Nghiên cứu phức chất phương pháp phổ khối lượng - 72 3.4 Nghiên cứu cấu trúc phức chất phương pháp phổ NMR - 75 3.4.1 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử H2L1 75 3.4.2 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II với dãy phối tử H2L2 - 82 3.4.3 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử H2L3 92 3.4.4 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử HL4 101 3.5 Nghiên cứu hoạt tính sinh học phối tử phức chất - 127 3.5.1 Hoạt tính kháng vi sinh vật phối tử phức chất 127 3.5.2 Khả ức chế phát triển tế bào ung thư phức chất - 127 3.6 Nghiên cứu mối tương quan cấu trúc - hoạt tính sinh học phức chất 130 KẾT LUẬN 139 NHỮNG ĐÓNG GÓP MỚI CỦA LUẬN ÁN - 140 TÀI LIỆU THAM KHẢO - 142 e DANH MỤC CÁC KÝ HIỆU, CHỮ VIẾT TẮT A549 Dòng ung thư biểu mô tế bào phổi (human lung adenocarcinoma epithelial cells line) CC Sắc kí cột (Columm Chromatography) CDCl3 Chloroform deuteri hóa DNA Deoxyribo Nucleic Acid DCM Dichlorometan DMSO Dung mơi dimethyl sulfoxide ESI-MS Phổ khối lượng phun mù điện tử (Electrospray Ionization Mass Spectrometry) EtOH Ethanol EtOAc Ethyl acetate H(%) Hiệu suất phản ứng (%) HCT-116 Dòng ung thư đại tràng (human colon carcinoma cell line) H2L Dãy phối tử dạng diimine N2O2, H nhóm OH HL Dãy phối tử dạng monoimine NO, H nhóm OH HL-60 Dòng ung thư tuyến tiền liệt (human leukemia cell line) HeLa Dịng tế bào ung thư biểu mơ (human epithelial carcinoma cell line) Hep-G2 Dòng tế bào ung thư gan (Human hepatocellular carcinoma cell line) HMBC Tương tác dị hạt nhân qua nhiều liên kết (Heteronuclear Multiple Bond Coherence) HSQC Tương tác dị hạt nhân qua liên kết (Heteronuclear Single Quantum Coherance) IR Phổ hồng ngoại (Infrared spectroscopy) IC50 Nồng độ chất thử ức chế 50% phát triển tế bào (Compound concentrations that produce 50% of cell growth inhibition) K562 Dòng tế bào ung thư máu cấp (Chronic myelogenous leukemic cell line) KB Lu Dòng tế bào ung thư biểu mô (Human epidemoid carcinoma cell line) Dòng tế bào ung thư phổi (Lung carcinoma cell line) f L Phối tử (Ligand) M Kim loại chuyển tiếp hóa trị M(II) (Transition Metal) MCF-7 Dịng tế bào ung thư vú (Human breast adenocarcinoma cell line) MeOH Metanol MIC Giá trị nồng độ ức chế tối thiểu (Minimum Inhibitory Concentration values) MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium N2O2 Phối tử bazơ Schiff dạng (diimine) NO Phối tử bazơ Schiff dạng (monoimine) P Phức chất (complex) PC3 Dòng tế bào ung thư tuyến tiền liệt (human prostate cancer cell line) Ph Nhóm phenyl rt Nhiệt độ phịng R Cấu hình (R) S Cấu hình (S) Salen Salicylaldehyde-ethylendiamine TLC Sắc kí lớp mỏng (Thin Layer Chromatography) TLTK Tài liệu tham khảo t-bu Nhóm tert-butyl br Broad d Mũi đơi (Doublet) dd Mũi đôi mũi đôi (Doublet of doublets) dm Nhiều mũi đôi (Doublet of multiplets) dt Doublet triplet m Nhiều mũi (Multiplet) ppm Phần triệu (Parts per million) q Mũi bốn (Quartet) s Mũi đơn (Singlet) t Mũi ba (Triplet) Phổ cộng hưởng từ hạt nhân proton proton 1H (Proton Nuclear H-NMR Magnetic Resonance spectroscopy) 13 C-NMR Phổ cộng hưởng từ hạt nhân carbon 13 (Carbon-13 Nuclear g Magnetic Resonance spectroscopy) J Hằng số tương tác spin-spin (Hz) Độ dịch chuyển hóa học (ppm) Ký hiệu 5ms Tên hóa học 5-methoxy-salicylaldehyde Cơng thức cấu tạo 3tbs 3-t-butyl-salicylaldehyde 5tbs 5-t-butyl-salicylaldehyde 3,5tbs 3,5-di-tert-butyl-salicylaldehyde 5Cls 5-chloro-salicylaldehyde 5Brs 5-bromo-salicylaldehyde 5Is 5-iodo-salicylaldehyde 5Fs 5-fluoro-salicylaldehyde H2spd N,N'-bis(salicylidene)-1,2phenylendiamine cis-H2scd N,N'-bis(salicylidene)cyclohexanediamine trans-H2scd N,N'-bis(salicylidene)- trans -1,2cyclohexanediamine cis-1,2- h H2sed N,N'-bis(salicylidene)-1,2ethylenediamine H25msed N,N'-bis(5-methoxy-salicylidene)1,2-ethylenediamine H23tbsed N,N'-bis(3-tert-butyl-salicylidene)1,2-ethylenediamine H25tbsed N,N'-bis(5-tert-butyl-salicylidene)1,2-ethylenediamine H23,5tbsed N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediamine H25Clsed N,N'-bis(5-chloro-salicylidene)1,2-ethylenediamine H25Brsed N,N'-bis(5-bromo-salicylidene)1,2-ethylenediamine H25Ised N,N'-bis(5-iodo-salicylidene)-1,2ethylenediamine H25Fsed N,N'-bis(5-fluoro-salicylidene)1,2-ethylenediamine (R)-Hspa (R)-N-salicylidene-1phenylethylamine (S)-N-salicylidene-1phenylethylamine (S)-Hspa (S)-H5mspa (S)-N-5-methoxy-salicylidene-1phenylethylamine i (R)-H5tbspa (R)-N-5-tert-butyl-salicylidene-1- (S)-H5tbspa phenylethylamine (S)-N-5-tert-butyl-salicylidene-1phenylethylamine (R)-H5Clspa (S)-H5Clspa (R)-N-5-chloro-salicylidene-1phenylethylamine (S)-N-5-chloro-salicylidene-1phenylethylamine (R)-H5Brspa (R)-N-5-bromo-salicylidene-1phenylethylamine (S)-H5Brspa (S)-N-5-bromo-salicylidene-1phenylethylamine (R)-H5Ispa (S)-H 5Ispa (R)-H5Fspa (S)-H5Fspa H2L1 H2L2 H2L3 HL4 (R)-N-5-iodo-salicylidene-1phenylethylamine (S)-N-5-iodo-salicylidene-1phenylethylamine (R)-N-5-fluoro-salicylidene-1phenylethylamine (S)-N-5-fluoro-salicylidene-1phenylethylamine Dãy phối tử dạng diimine N2O2: H2spd, cis-H2scd, transH2scd Dãy phối tử N2O2: H2sed; H25msed, H23tbsed, H25tbsed, H23,5tbsed Dãy phối tử N2O2: H25Clsed, H25Brsed, H25Ised; H25Fsed Dãy phối tử NO: (R)- (S)-Hspa, (S)-H5mspa, (R)- (S)H5tbspa, (R)- (S)-H5Clspa, (R)- (S)-H5Brspa, (R)- (S)H5Ispa, (R)- (S)-H5Fspa j DANH MỤC BẢNG Bảng 1.1 Phức chất kim loại M(II) với phối tử từ dẫn xuất salicylaldehyde với 1,3-propanediamine Bảng 1.2 Phức chất kim loại M(II) với phối tử từ dẫn xuất salicylaldehyde dẫn xuất 1,2-ethylenediamine Bảng 1.3 Phức chất kim loại M(II) với phối tử từ dẫn xuất salicylaldehyde với dẫn xuất 1,2-phenylenediamine Bảng 1.4 Phức chất Cu(II) với phối tử 3,5-di-tert-butyl salicylaldehyde 19 Bảng 1.5 Phức chất Cu(II) với phối tử từ dẫn xuất salicylaldehyde [105] 19 Bảng 2.1 Hóa chất dung môi 29 Bảng 2.2 Hiệu suất tổng hợp màu sắc dẫn xuất salicylaldehyde 31 Bảng 2.3 Hiệu suất màu sắc phối tử bazơ Schiff dạng 34 Bảng 2.4 Hiệu suất tổng hợp màu sắc phối tử bazơ Schiff NO 40 Bảng 2.5 Hiệu suất tổng hợp màu sắc phức chất với phối tử 48 Bảng 2.6 Hiệu suất tổng hợp màu sắc phức chất với phối tử 57 Bảng 3.1 Các dải dao động đặc trung phổ IR phối tử phức chất dạng N2O2 dãy H2L1; H2L2; H2L3 (ν, cm-1) 68 Bảng 3.2 Các dải dao động đặc trung phổ IR phối tử phức chất dạng dãy HL4 (ν, cm-1) 70 Bảng 3.3 Mảnh ion phân tử phổ khối lượng phối tử phức chất 72 Bảng 3.4 Dữ liệu phổ NMR phối tử 110 phức chất 121a, 121b 77 Bảng 3.5 Dữ liệu phổ NMR phối tử 111a phức chất 122a, 122b 79 Bảng 3.6 Dữ liệu phổ NMR phối tử 111b phức chất 122c, 122d 80 Bảng 3.7 Dữ liệu phổ NMR phối tử 112a phức chất 123a, 123b 83 Bảng 3.8 Dữ liệu phổ NMR phối tử 112b phức chất 124a, 124b 85 Bảng 3.9 Dữ liệu phổ NMR phối tử 112d phức chất 126a, 126b 85 Bảng 3.10 Dữ liệu phổ NMR phối tử 112c phức chất 125a, 125b 88 Bảng 3.11 Dữ liệu phổ NMR phối tử 112e phức chất 127 89 Bảng 3.12 Dữ liệu phổ NMR phối tử 112i phức chất 131 96 Bảng 3.13 Dữ liệu phổ NMR phối tử 112f phức chất 128a, 128b 97 Bảng 3.14 Dữ liệu phổ NMR phối tử 112g phức chất 129a, 129b 98 Bảng 3.15 Dữ liệu phổ NMR phối tử 112f phức chất 130a, 130b 99 k [14] [15] [16] [17] [18] [19] [20] [21] [22] Prieto, Virtudes Moreno, Synthesis and characterization of palladium(II) and platinum(II) complexes with Schiff bases derivatives of 2-pyridincarboxy aldehyde Study of their interaction with DNA, Journal of Inorganic Biochemistry, 2006, 100, 1368–1377 Omima M.I Adly, Ali Taha, Shery A Fahmy, Synthesis, spectral characterization, molecular modeling and antimicrobial activity of new potentially N2O2 Schiff base complexes, Journal of Molecular Structure, 2013, 1054–1055, 239–250 Magdy Shebl, Synthesis, spectroscopic characterization and antimicrobial activity of binuclear metal complexes of a new asymmetrical Schiff baseligand: DNA binding affinity of copper(II) complexes, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 117, 127–137 Ayman A Abdel Aziz, Synthesis, spectroscopic characterization, thermal studies, catalytic epoxidation and biological activity of chromium and molybdenum hexacarbonyl bound to a novel N2O2 Schiff base, Journal of Molecular Structure, 2010, 979, 77–85 Ayman A Abdel Aziz, Ibrahim H.A Badr, Ibrahim S.A El-Sayed, Synthesis, spectroscopic, photoluminescence properties and biological evaluation, of novel Zn(II) and Al(III) complexes of NOON tetradentate Schiff bases, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, 97, 388–396 M Sivasankaran Nair, D Arish, J Johnson, Synthesis, characterization and biological studies on some metal complexes with Schiff base ligand containing pyrazolone moiety, Journal of Saudi Chemical Society, 2016, 20 (1), S591–S598 Abhay Nanda Srivastva, Netra Pal Singh, Chandra Kiran Shriwastaw, In vitro antibacterial and antifungal activities of binuclear transition metal complexes of ONNO Schiff base and 5-methyl-2,6-pyrimidine-dione and their spectroscopic validation, Arabian Journal of Chemistry, 2016, 9, 48-61 Kanne Shanker, Rondla Rohini, Vadde Ravinder, P Muralidhar Reddy, YenPeng Ho, Ru(II) complexes of N4 and N2O2 macrocyclic Schiff base ligands: Their antibacterial and antifungal studies, Spectrochimica Acta Part A, 2009, 73, 205–211 Mehmet Turner, Duygu Ekinci, Ferhan Tumer, Akif Bulut, Synthesis, characterization and properties of some divalent metal(II) complexes: Their electrochemical, catalytic, thermal and antimicrobial activity studies, Spectrochimica Acta Part A, 2007, 67, 916–929 Yousif, Emad, Rentschler, Eva, Salih, Nadia, Salimon, Jumat, Hameed, Ayad, Katan, Mustafa, Synthesis and antimicrobial screening of tetra Schiff bases of 1,2,4,5-tetra (5-amino-1,3,4-thiadiazole-2-yl)benzene, Journal of Saudi 143 [23] [24] [25] [26] [27] [28] [29] [30] [31] [32] Chemical Society, 2014, 18, 269–275 A.A Abou-Hussein, Wolfgang Linert, Synthesis, spectroscopic studies and inhibitory activity against bactria and fungi of acyclic and macrocyclic transition metal complexes containing a triamine coumarine Schiff base ligands, Spectrochimica Acta Part A, 2015, 141, 223–232 Lei Xia, Yu-Fen Xia, Li-Rong Huang, Xiao Xiao, Hua-yong Lou, TangJingjun Liu, Wei-Dong Pan, Heng Luo, Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structureemicrobicidal activity relationship, European Journal of Medicinal Chemistry, 2015, 97, 83–93 M.L Sundararajan, T Jeyakumar, J Anandakumaran, B Karpanai Selvan, Synthesis of metal complexes involving Schiff base ligand with methylenedioxy moiety: Spectral, thermal, XRD and antimicrobial studies, Spectrochimica Acta Part A, 2014, 131, 82–93 Kaushik Ghosh, Nidhi Tyagi, Pramod Kumar, Udai P Singh, Nidhi Goel, Stabilization of Mn(II) and Mn(III) in mononuclear complexes derived from tridentate ligands with N2O donors: Synthesis, crystal structure, superoxide dismutase activity and DNA interaction studies, Journal of Inorganic Biochemistry, 2010, 104, 9–18 Omyma A.M Ali, Palladium(II) and zinc(II) complexes of neutral [N O ] donor Schiff bases derived from furfuraldehyde: Synthesis, characterization, fluorescence and corrosion inhibitors of ligands, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 132, 52–60 Evan B Douple, Cis-diamminedichloroplatinum(II): Effects of a representtative metal coordination complex on mammalian cells Pharmac Ther 1984, 25, 297–326 Sun, Yanyan, Liu, Fei, Gou, Shaohua, Cheng, Lin, Fang, Lei, Yin, Runting, Synthesis and in vitro antiproliferative activity of platinum(II) complexes with N-monoalkyl 1R,2R-diaminocyclohexane as ligands, European Journal of Medicinal Chemistry, 2012, 55, 297–306 Jennifer S Butler and Peter J Sadler, Targeted delivery of platinum-based anticancer complexes, Chemical Biology, 2013, 17,175–188 Mozaffar Asadi, Zahra Asadi, Leila Zarei, Somaye Barzegar Sadi, Zahra Amirghofran, Affinity to bovine serum albumin and anticancer activity of some new water-soluble metal Schiff base complexes, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 133, 697–706 Zoran D Matovíc Emina Mrkalíc, Gordana Bogdanovíc, Vesna Kojíc, Auke Meetsma, Ratomir Jelíc, Antitumor effects of a tetradentate amidocarboxylate ligands and corresponding square-planar palladium(II) 144 [33] [34] [35] [36] [37] [38] [39] [40] [41] complexes toward some cancer cells Crystal structure, DFT modeling and ligand to DNA probe Docking simulation, Journal of Inorganic Biochemistry, 2013, 121, 134–144 Gehad G Mohamed, Ehab M Zayed, Ahmed M.M Hindy, Coordination behavior of new bis Schiff base ligand derived from 2-furan carboxaldehyde and propane-1,3-diamine Spectroscopic, thermal, anticancer and antibacterial activity studies, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 145, 76–84 Tummalapalli KiranVuppalapati Giri Prasanth, Synthesis, spectroscopic characterization and in-vitro studies of new heteroleptic copper (II) complexes derived from 2-hydroxy napthaldehyde Schiff's bases and N, N donor phối tửs: Antimicrobial, DNA binding and cytotoxic investigations, Inorganica Chimica Acta, 2015, 433, 26-34 Natarajan Raman, Narayanaperumal Pravin, DNA fastening and ripping actions of novel Knoevenagel condensed dicarboxylic acid complexes in antitumor journey, European Journal of Medicinal Chem, 2014, 80, 57–70 Ahmed M Mansour, M.F Mohanied, Complexes of N-(2-thiazolyl)-1Hbenzotriazole-1-carbothioamide with Pd(II), Pt(II), and Zn(II): Spectral, DFT, cytotoxicity and anti-angiogenic effect on MCF-7 cell line, Inorganica Chimica Acta, 2014, 423, 373–383 Sze Koon Lee, Kong Wai Tan, Seik Weng Ng, Kah Kooi Ooi, Kok Pian Ang, Md Akim Abdah, Zinc (II) complex with a cationic Schiff base ligand: Synthesis, characterization, and biological studies, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 121, 101–108 Kuheli Das, Amitabha Datta, Pei-Hsin Liu, Jui-Hsien Huang, Chin-Lin Hsu, Barbara Machura, Chittaranjan Sinha, Wei-Tang Chang, Structural characterization of cobalt(II) complexes of an N,O donor Schiff base and their activity on carcinoma cells, Polyhedron, 2014, 71, 85–90 G.Y Nagesh, B.H.M Mruthyunjayaswamy, Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen and oxygen (ONO) donor Schiff base ligand derived from thiazole and 2-hydroxy1-naphthaldehyde, Journal of Molecular Structure, 2015, 1085, 198–206 Nour T Abdel Ghani, Palladium(II) and platinum(II) complexes containing benzimidazole ligand: Molecular structures, vibrational frequencies and cytotoxicity, Journal of Molecular Structure, 2011, 991, 108–126 Dimitra Kovala-Demertzi, Mavroudis A Demertzis, J.R Miller , Cryshanthi, Papadopoulou, Catherine Dodorou, Giorge Filousis, Platinum(II) complexes with 2-acetyl pyridine thiosemicarbazone Synthesis, crystal structure, spectral properties, antimicrobial and antitumour activity, Journal of Inorganic Biochemistry, 2001, 86, 555–563 145 [42] Wael Hussein Hegazy, Spectroscopic, thermal characterization and cytotoxic activity of bi-, tri- and tetra-nuclear Pd(II) and Pt(II) complexes with di Schiff base ligand, Journal of Molecular Structure, 2014, 1075, 103–112 [43] William M Motswainyana, Martin O Onani, Abram M Madiehe, Morounke Saibu, Ntevheleni Thovhogi, Roger A Lalancette, Imino-phosphine palladium(II) and platinum(II) complexes: Synthesis, molecular structures and evaluation as antitumor agents, Journal of Inorganic Biochemistry, 2013, 129, 112–118 [44] Gehad G Mohamed, M.M Omar, Amr A Ibrahim, Biological activity of palladium(II) and platinum(II) complexes of the acetone Schiff bases of Smethyl- and S-benzyldithiocarbazate and the X-ray crystal structure of the [Pd(asme)2] (asme=anionic form of the acetone Schiff base of Smethyldithiocarbazate) complex, Journal of Inorganic Biochemistry, 2002, 92, 141–148 [45] S.A Sadeek, M.S El-Attar, S.M Abd El-Hamid Preparation and characterization of new tetradentate Schiff base metal complexes and biological activity evaluation Journal of Molecular Structure, 2013, 1051, 30–40 [46] V Selvarani, B Annaraj, M.A Neelakantan, S Sundaramoorthy, D Velmurugan, Synthesis, characterization and crystal structures of copper(II) and nickel(II) complexes of propargyl arm containing N2O2 ligands: Antimicrobial activity and DNA binding, Polyhedron, 2013, 54, 74–83 [47] Tudor Rosu, Elena Pahontu, Catalin Maxim, Rodica Georgescu, Nicolae Stanica, Aurelian Gulea, Some new Cu(II) complexes containing an ON donor Schiff base: Synthesis,characterization and antibacterial activity, Polyhedron, 2011, 30, 154–162 [48] Cemal Şenol, Zeliha Hayvali, Hakan Dal, Tuncer Hökelek, Syntheses, characterizations and structures of NO donor Schiff base ligands and nickel(II) and copper(II) complexes, Journal of Molecular Structure, 2011, 997, 53–59 [49] Xiongwei Dong, Yuguang Li, Zuowen Li, Yongming Cui, Hailiang Zhu, Synthesis, structures and urease inhibition studies of copper(II) and nickel(II) complexes with bidentate N,O-donor Schiff base ligands, Journal of Inorganic Biochemistry, 2012, 108, 22–29 [50] Tingting Li, Yong Chen, Wen-Fu Fua, Photocatalytic H2 production from water based on platinum(II) Schiff base sensitizers and a molecular cobalt catalyst, Catalysis Communications, 2014, 45, 91–94 [51] Mahmut Ulusoy, Özgül Birel, Onur Sahin, Orhan Büyükgüngör, Bekir Cetinkaya, Structural, spectral, electrochemical and catalytic reactivity studies of a series of N2O2 chelated palladium(II) complexes, Polyhedron, 146 [52] [53] [54] [55] [56] [57] [58] [59] [60] [61] [62] 2012, 38, 141–148 Daver M Boghaei and Sajjad Mohebi, Non-symmetrical tetradentate vanadyl Schiff base complexes derived from 1,2-phenylenediamine and 1,3naphthalene diamine as catalysts for the oxidation of cyclohexene, Tetrahedron, 2002, 58, 5357–5366 S Sujarani, A Ramu, Docking of ethanamine Schiff base imines & metal (II) complexes,cytotoxicity & DNA interaction studies, Journal of Molecular Structure, 2015, 1079, 353–362 M.R Bermejo, A.M Gonzalez, M Fondo, M Maneiro, M Rey, M Vazquez, O.L Hoyos, J.C Garcıa-Monteagudo, Electrochemical synthesis of neutral Mn(III) complexes with asymmetrical N2O2 Schiff base ligands, Inorganica Chimica Acta, 2000, 307, 106–114 Alparslan Atahan, Sefa Durmus, 1-Amino-2-hydroxy-4-naphthalenesulfonic acid based Schiff bases or naphtho[1,2-d]oxazoles: Selective synthesis and photophysical Properties, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 144, 61–67 D.M Kweeke et al., Pharmacology of oxaliplatin and the use pharmacoge nomics to individualize therapy Cancer Treatment Reviews, 2005, 31, 90– 105 B Rosenberg, L Van Camp, J E Trosko and V.H Mansour, Platinum Compounds: a New Class of Potent Antitumour Agents, Nature, 1969, 222, 385–386 Bernard Desoize, Claudie Madoulet, Particular aspects of platinum compounds used at present in cancer treatmen, critical reviews in oncology/hematology, 2002, 42, 317–325 Shaloam Dasari, Paul Bernard Tchounwou, Review cis-platin in cancer therapy: Molecular mechanisms of action European Journal of Pharmacology, 2014, 740, 364–378 Mehmet Sưnmez, Metin Çelebi, Yavuz Yardım, Zühre Şentürk, Palladium(II) and platinum(II) complexes of a symmetric Schiff base derived from 2,6,diformyl-4-methylphenol with N-aminopyrimidine: Synthesis, characterization and detection of DNA interaction by voltammetry, European Journal of MedicinalChemistry, 2010, 45, 4215–4220 V Selvarani, B Annaraj, M.A Neelakantan, S Sundaramoorthy, D Velmurugan, Synthesis and crystal structure of hydroxyacetophenone Schiff bases containing propargyl moiety: Solvent effects on UV-visible spectra, Spectrochimica Acta Part A, 2012, 91, 329–337 S S Sreejith, S.S Sreejith, Nithya Mohan, N Aiswarya, M.R Prathapachandra Kurup, Inclusion, pseudo-inclusion compounds and coordination polymer of Pd(II), Zn(II) and Cd(II) from salen-type Schiff base 147 [63] [64] [65] [66] [67] [68] [69] [70] [71] [72] ligand with a 1,3-diimino spacer group: Crystal structures, spectroscopic and thermal studies, Polyhedron, 2016, 115, 180–192 Beata Cristóvão, Barbara Miroslaw, Julia Kłak, New mononuclear CuII and tetranuclear CuII2–LaIII2 Schiff base complexes – Physicochemical properties, Polyhedron, 2013, 62, 218–226 Seema Yadav, Musheer Ahmad, K.S Siddiqi Metal-ion directed synthesis of N2O2 type chelate complexes of Ni(II), Cu(II) and Zn(II): Spectral, thermal and single crystal studies, Spectrochimica Acta Part A, 2012, 98, 240–246 Monami Maiti, Dipali Sadhukhan, Santarupa Thakurta, Ennio Zangrando, Antonio Bauzá, Antonio Frontera, Bülent Dede, Samiran Mitra, Guillaume Pilet, Synthesis, structural characterization, theoretical calculations and catecholase mimetic activity of manganese-Schiff base complexes, Polyhedron, 2014, 75, 40–49 Hiroto Achira, Yuki Hoga, Isao Yoshikawa, Toshiki Mutai, Kazunari Matsumura, Hirohiko Houjou, Effects of a semiflexible linker on the mechanochromic photoluminescence of bis(Pt-salen) complex, Polyhedron, 2016, 113, 123–131 Ali Ourari, Djouhra Aggoun, Lahcène Ouahab, A novel copper(II)-Schiff base complex containing pyrrole ring: Synthesis, characterization and its modified electrodes applied in oxidation of aliphatic alcohols, Inorganic Chemistry Communications, 2013, 33, 118–124 Leon Dyers Jr., Steven Y Que, Donald Van Derveer, Xiu R Bu, Synthesis and structures of new salen complexes with bulky groups, Inorganica Chimica Acta, 2006, 359, 197–203 Abdel-Nasser M.A Alaghaz, Yousry A Ammar, Hoda A Bayoumi, Sharah A Aldhlmani, Synthesis, spectral characterization, thermal analysis, molecular modeling and antimicrobial activity of new potentially N2O2 azodye Schiff base complexes, Journal of Molecular Structure, 2014, 1074, 359– 375 D Tomczyk, L Nowak, W Bukowski, K Bester, P Urbaniak, G Andrijewski, B Olejniczak, Reductive and oxidative electrochemical study and spectroscopic properties of nickel(II) complexes with N2O2 Schiff bases derived from (±)-trans-N,N-2-bis(salicylidene)-1,2-cyclohexanediamine, Electrochimica Acta, 2014, 121, 64– 77 W Schilf, B Kamienski, Z Rozwadowski, K Ambroziak, B Bieg, T Dziembowska, Solid state 15N and 13C NMR study of dioxomolybdenum (VI) complexes of Schiff bases derived from trans-1,2-cyclohexanediamine, Journal of Molecular Structure, 2004, 700, 61–65 Maria Proetto, Wukun Liu, Adelheid Hagenbach, Ulrich Abram, Ronald Gust, Synthesis, characterization and in vitro antitumour activity of a series 148 [73] [74] [75] [76] [77] [78] [79] [80] [81] of novel platinum(II) complexes bearing Schiff base ligands, European Journal of Medicinal Chemistry, 2012, 53, 168–175 Akmal S Gaballa, Mohsen S Asker, Atiat S Barakat, Said M Teleb, Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from salicylaldehyde, 2-furaldehyde and phenylenediamine, Spectrochimica Acta Part A, 2007, 67, 114–121 Mohamed I Ayad, Synthesis, characterization and catechol oxidase biomimetic catalytic activity of cobalt(II) and copper(II) complexes containing N2O2 donor sets of imine ligands, King Saud University Arabian Journal of Chemistry, 2016, (2), S1297–S1306 Ali Hossein Kianfar, Liala Keramat, Morteza Dostani, Mojtaba Shamsipur, Mahmoud Roushani, Farzad Nikpour, Synthesis, spectroscopy, electrochemistry and thermal study of Ni(II) and Cu(II) unsymmetrical N2O2 Schiff base complexes, Spectrochimica Acta Part A, 2010, 77, 424–429 Khosro Mohammadi, Mahmood Niad, Tahereh Jafari, New 3,4-diaminobenzoic acid Schiff base compounds and their complexes: Synthesis, characterization and thermodynamics, Spectrochimica Acta Part A, 2014, 122, 179– 185 Ying-Zhong Shen, Yi Pan, Le-Yong Wang, Gang Dong, Xiao-Ping Jin, XiaoYing Huang, Hongwen Hu, Synthesis and characterisation of alkyl-N,N’bis(salicylidene)ethylenediamino- and alkyl-N,N’-bis(salicylidene)-1,2-phenyl enediaminogallium or indium complexes: crystal structure of methyl-N,N’bis(salicylidene)-1,2-phenylenediaminoindium, Journal of Organo- metallic Chemistry, 1999, 590, 242–247 Yan Chen, YaojuLiu, Xingmei Zhang, Zhao Zhang, Lin Liu, Daidi Fan, LiqinDing, Xingqiang Lü, Stereo-regulated methyl methacrylate (MMA) polymerization catalyzed by asymmetric Salen-type Schiff-base Cu(II) complexes, Inorganic Chemistry Communications, 2015, 53, 1–3 Christopher T Lyons, T Daniel P Stack Recent advances in phenoxyl radical complexes of salen-type ligands as mixed-valent galactose oxidase models, Coordination Chemistry Reviews, 2013, 257, 528–540 Liqin Ding, Zeng Chu, Leilei Chen, Xingqiang Lü, Biao Yan, Jirong Song, Daidi Fan, Feng Bao, Pd-Salen and Pd-Salan complexes: Characterization and application instyrene polymerization, Inorganic Chemistry Communications, 2011, 14, 573–577 Jie Zhang, Guoliang Dai, Fengshou Wu, Dan Li, Dongchun Gao, Haiwei Jin, Song Chen, Xunjin Zhu, Chenxiu Huang, Deman Han, Efficient and tunable phosphorescence of new platinum(II) complexes based on the donor–π– acceptor Schiff bases, Journal of Photochemistry and Photobiology A: Chemistry, 2016, 316, 12–18 149 [82] Joana Fonseca, Javier Martinez, Luís Cunha-Silva, Alexandre L Magalhães, M Teresa Duarte, Cristina Freire, Insights into electronic and structural properties of novel Pd(II) salen-type complexes, Inorganica Chimica Acta, 2010, 363, 4096–4107 [83] Mozaffar Asadi, Zahra Asadi, Leila Zarei, Somaye Barzegar Sadi, Zahra Amirghofran, Affinity to bovine serum albumin and anticancer activity of some new water-soluble metal Schiff base complexes, Spectrochimica Acta Part A, 2014, 133, 697–706 [84] Elham S Aazam, Waleed Ahmed El-Said Synthesis of copper/nickel nanoparticles using newly synthesized Schiff-base metals complexes and their cytotoxicity/catalytic activities, Bioorganic Chemistry, 2014, 57, 5–12 [85] Noor-ul Hasan Khan, Nirali Pandya, K Jeya Prathap, Rukhsana Ilays Kureshy, Sayed Hasan Razi Abdi, Sandhya Mishra, Hari Chandra Bajaj, Chiral discrimination asserted by enantiomers of Ni(II), Cu(II) and Zn(II) Schiff base complexes in DNA binding, antioxidant and antibacterial activities, Spectrochimica Acta Part A, 2011, 81, 199–208 [86] Soleiman Hisaindee, Rabah Iratni, Leena Al-Kaabi, Na’il Saleh, Suad Ajeb, Synan F AbuQamar, Yaser Torky, Antipathogenic effects of structurallyrelated Schiff base derivatives: Structure–activity relationship, Arabian Journal of Chemistry, 2015, 8, 828–836 [87] Cleiton M da Silva, Daniel L da Silva, Luzia V Modolo, Rosemeire B Alves, Maria A de Resende, Cleide V.B Martins, Angelo de Fatima, Schiff bases: A short review of their antimicrobial activities, Journal of Advanced Research, 2011, 2, 1–8 [88] Muhammad Shabbir, Zareen Akhter, Iqbal Ahmad, Safeer Ahmed, Hammad Ismail, Bushra Mirza, Vickie McKee, Copper (II) complexes bearing ether based ON donor bidentate Schiff bases: Synthesis, characterization, biological and electrochemical investigations, Polyhedron, 2017, 124, 117– 124 [89] Zahra Kazemi, Hadi Amiri Rudbari, Mehdi Sahihi, Valiollah Mirkhani, Majid Moghadam, Sharam Tangestaninejad, Iraj Mohammadpoor-Baltork, Gholamhassan Azimi, Sajjad Gharaghani, Abolghasem Abbasi Kajani Synthesis, characterization and separation of chiral and achiral diastereomers of Schiff base Pd(II) complex: A comparative study of their DNA- and HSA-binding, Journal of Photo chemistry & Photobiology, B: Biology 2016, 163, 246–260 [90] Zhen Li, Hui Yan, Guoliang Chang, Min Hong, Jianmin Dou, Meiju Niu, Cu(II), Ni(II) complexes derived from chiral Schiff-base ligands: Synthesis, characterization, cytotoxicity, protein and DNA–binding properties, Journal of Photochemistry & Photobiology, B: Biology, 2016, 163, 403–412 150 [91] [92] [93] [94] [95] [96] [97] [98] [99] Eliene Leandro de Arẳjo, Hellen Franciane Gonc¸ alves Barbosa, Edward Ralph Dockal, Éder Tadeu Gomes Cavalheiro, Synthesis, characterization and biological activity of Cu(II), Ni(II) and Zn(II) complexes of biopolymeric Schiff bases of salicylaldehydes and chitosan, International Journal of Biological Macromolecules, 2017, 95, 168–176 Alyssa E Patterson, Jessica J Miller, Brittany A Miles, Erin L Stewart, Josée-Marie E.J Melanson, Christopher M Vogels, Amanda M Cockshutt, Andreas Decken, Pier Morin Jr., Stephen A Westcott, Synthesis, characterization and anticancer properties of (salicylaldiminato)platinum(II) complexes, Inorgani fca Chimica Acta, 2014, 415, 88–94 Mohamed Ramadan El Sayed Aly, Hamadah Hamadah Abd El Razek Fodah, Sherif Yousef Saleh, Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes, European Journal of Medicinal Chemistry, 2014, 76, 517–530 Halime Güzin Aslan, Servet Özcan, Nurcan Karacan, Synthesis, characterization and antimicrobial activity of salicylaldehyde benzenesulfonylhydrazone (Hsalbsmh) and its Nickel(II), Palladium(II), Platinum(II), Copper(II), Cobalt(II) complexes, Inorganic Chemistry Communications, 2011, 14, 1550–1553 Meiju Niu, Min Hong, Guoliang Chang, Xiao Li, Zhen Li, A comparative study of cytotoxicity and interaction with DNA/protein offive transition metal complexes with Schiff base ligands, Journal of Photochemistry and Photobiology B: Biology, 2015, 148, 232–241 C.E Satheesh, P Raghavendra Kumar, P Sharma, K Lingaraju, B.S Palakshamurthy, H Raja Naika, Synthesis, characterisation and antimicrobial activity of new palladium and nickel complexes containing Schiff bases, Inorganica Chimica Acta, 2016, 442, 1–9 Reyhan Kag it, Osman Dayan, Namik Özdemir, Palladium(II) and Ruthenium(II complexes bearing arylsulfonate based ligands: synthesis, structural characterization and catalytic properties, Polyhedron, 2016, 117, 504–512 Hadi Amiri Rudbari, Mohammad Reza Iravani, Vahid Moazam, Banafshe Askari, Mahsa Khorshidifard, Neda Habibi, Giuseppe Bruno, Synthesis, characterization, X-ray crystal structures and antibacterial activities of Schiff base ligands derived from allylamine and their vanadium(IV), cobalt(III), nickel(II), copper(II), zinc(II) and palladium(II) complexes, Journal of Molecular Structure, 2016, 1125, 113–120 Mahsa Khorshidifard, Hadi Amiri Rudbari, Zahra Kazemi-Delikani, Valiollah Mirkhani, Reza Azadbakht Synthesis, characterization and X-ray crystal structures of Vanadium(IV), Cobalt(III), Copper(II) and Zinc(II) complexes 151 [100] [101] [102] [103] [104] [105] [106] [107] [108] derived from an asymmetric bidentate Schiff-base ligand at ambient temperature, Journal of Molecular Structure, 2015, 1081, 494–505 S.M Pradeepa, H.S Bhojya Naik , B Vinay Kumar, K Indira Priyadarsini, Atanu Barik, M.C Prabhakara, DNA binding, photoactivated DNA cleavage and cytotoxic activity of Cu(II) and Co(II) based Schiff-base azo photosensitizers, Spectrochimica Acta Part A, 2015, 141, 34–42 Mukul Kalita, Kashyap Jyoti Tamuli, Pranjit Barman, Bipul Sarma, Reshita Baruah, Hari Prasanna Deka Boruah, Synthesis, crystal structure, bioactivities of Ni(II), Cu(II), Co(II) and Pd(II) complexes with unsymmetrical thioether donor Schiff base: Phosphinefree Pd(II) complex catalyzed Suzuki reaction, Polyhedron, 2015, 97, 140–147 Emad Yousif, Jumat Salimon, Ahmed Majeed, Bashar Abdullah, Khulood Al-Sammarrae, Nadia Salih, Metal complexes of Schiff base: Preparation, characterization and antibacterial activity, Arabian Journal of Chemistry, 2017, 10, S1639–S1644 V.T Kasumov, F Suzergoz, E Sahin, O Celik, M Aslanoglu, Synthesis, characterization and effect of the fluorine substitution on the redox reactivity and in vitro anticancer behaviors of N-polyfluorophenyl-3,5-di-tert butylsalicylaldimines and their Cu(II) complexes, Journal of Fluorine Chemistry, 2014, 162, 78–89 Veli T Kasumov, Seniz Ozalp-Yaman, Esref Tas¸ Synthesis, spectroscopy and electrochemical behaviors of nickel(II) complexes with tetradentate shiff bases derived from 3,5-But2-salicylaldehyde, Spectrochimica Acta Part A, 2005 62, 716–720 Yongming Cui, Xiongwei Dong, Yuguang Li, Zuowen Li, Wu Chen, Synthesis, structures and urease inhibition studies of Schiff base metal complexes derived from 3,5-dibromosalicylaldehyde, European Journal of Medicinal Chemistry, 2012, 58, 323–331 S Jone Kirubavathy, R Velmurugan, R Karvembu, N.S.P Bhuvanesh, Israel V.M.V Enoch, P Mosae Selvakumar, D Premnath, S Chitra, Structural and molecular docking studies of biologically active mercaptopyrimidine Schiff bases, Journal of Molecular Structure, 2017, 1127, 345–354 Lei Shi, Hui-Ming Ge, Shu-Hua Tan, Huan-Qiu Li, Yong-Chun Song, HaiLiang Zhu, Ren-Xiang Tan, Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde, European Journal of Medicinal Chemistry, 2007, 42, 558–564 Ahmed Nuri Kursunlu, Ersin Guler, Fatih Sevgi, Birol Ozkalp, Synthesis, spectroscopic characterization and antimicrobial studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Schiff bases derived from 5-bromosalicylaldehyde, Journal of Molecular Structure, 2013, 1048, 476–481 152 [109] Serenella Medici, Massimiliano Peana, Valeria Marina Nurchi, Joanna I Lachowicz, Guido Crisponi, Maria Antonietta Zoroddu, Noble metals in medicine: Latest advances, Coordination Chemistry Reviews, 2015, 284, 329–350 [110] Runting Yin, Shaohua Gou, Xia Liu, Liguang Lou Antitumor activities and interaction with DNA of oxaliplatin-type platinum complexes with linear or branched alkoxyacetates as leaving groups, Inorganic Biochemistry, 2011, 105, 1095–1101 [111] C Monneret, General Review Platinum anticancer drugs From serendipity to rational design, Annales Pharmaceutiques Franỗaises, 2011, 69, 286295 [112] A M Di Francesco, A Ruggiero and R Riccardi, Drugs of the Future: Review Cellular and molecular aspects of drugs of the future: Oxaliplatin CMLS Cellular and Molecular Life Sciences, 2002, 59, 1914–1927 [113] Lloyd R Kelland New platinum antitumor complexes, Critical Reviews in Oncology/Hematology, 1993, 15, 191–219 [114] Federica Trudu, Filippo Amato, Petr Vanhara, Tiziana Pivetta, E.M Peña-ra Méndez, Josef Havel, Coordination compounds in cancer: Past, present and perspectives, Journal of applied biomedicine, 2015 , 13, 79–103 [115] Tim Mosmann Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assay Journal of immunological methods, 1983, 65, 55–63 [116] Scudiero D.A., Evaluation of a soluable tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines Cancer Reseach 1988, 48: 4827–4833 [117] Cos P, Vlietinck AJ, Vanden BD, Maes L Anti-infective potential of nature products: How to develop a stronger in vitro ‘proof-of-concept’ Journal of Ethnopharmacology, 2006, 106 (3), 290–302 [118] Pual Cos, et al., Bioassay for antibacterial and antifungal activities, Laboratory for Microbiology, Parasitology and Hygien, Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, Belgium, 2005, 1–13 [119] Franz Hadacek, Harald Greger Testing of Antifungal Natural Products: Methodologies, Comparability of Results and Assay Choice, Phytochemical analysis, 2000, 11, 137–147 [120] G Tweedy, Possible mechanism for reduction of elemental sulfur by monilinia fructicola, Phytopathology, 1964, 55, 910–914 [121] Yu-Xing Tan, Zhi-Jian Zhang, Yang Liu, Jiang-Xi Yu, Xiao-Ming Zhu, DaiZhi Kuang, Wu-Jiu Jiang, Synthesis, crystal structure and biological activity of the Schiff base organotin(IV) complexes based on salicylaldehyde-oaminophenol, Journal of Molecular Structure, 2017, 1149, 874–881 153 [122] MohammadMehdi Haghdoost, Golara Golbaghi, Myriam Letourneau, Shunmoogum A Patten, Annie Castonguay, Lipophilicity-antiproliferative activity relationship study leads to the preparation of a ruthenium(II) arene complex with considerable in vitro cytotoxicity against cancer cells and a lower in vivo toxicity in zebrafish embryos than clinically approved cis-platin, European Journal of Medicinal Chemistry, 2017, 132, 282–293 [123] Jee-Young Lee, Min-Cheol Jeong, Dasom Jeon, Yeongjun Lee, Woo Cheol Lee, Yangmee Kim, Structure-activity relationship-based screening of antibiotics agains Gram-negative Acinetobacter baumannii, Bioorganic & Medicinal Chemistry, 2017, 25, 372–380 [124] Chandravadivelu Gopi, Vedula Girija Sastry, Magharla Dasaratha Dhanaraju, Synthesis, spectroscopic characterization, X-ray crystallography, structural activity relationship and antimicrobial activity of some novel 4-(5-(10-(3-N, N-dimethylamino)propyl)-10H-phenothiazine3-yl)-1,3,4-thiadiazole-2-yl) Azo dye/Schiff base derivatives, Future Journal of Pharmaceutical Sciences, 2017, 3, 79–89 [125] Chandravadivelu Gopi, Vedula Girija Sastry, Magharla Dasaratha Dhanaraju, Microwave-assisted synthesis, structural activity relationship and biological activity of some new quinoxaline Schiff base derivatives as highly potent spirochete bactericidal agents, Beni-Suef University Journal of Basic and Applied Sciences 2017 6, 39–47 [126] Sayan Dutta Gupta, B Revathi, Gisela I Mazaira, Mario D Galigniana, C.V.S Subrahmanyam, N.L Gowrishankar, N.M Raghavendra, 2,4dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead, Bioorganic Chemistry 2015, 59, 97–105 [127] Krzysztof Sztanke, Agata Maziarka, Anna Osinka, Malgorzata Sztanke, An insight into synthetic Schiff bases revealing antiproliferative activities in vitro, Bioorganic & Medicinal Chemistry, 2013, 21, 3648–3666 [128] Kannan Balan, Periyasamy Ratha, Govindan Prakash, Periyasamy Viswanathamurthi, Thayumanavan Palvannan, Sirichai Adisakwattana, Evaluation of invitro α-amylase and α-glucosidase inhibitory potential of N2O2 schiff base Zn complex, Arabian Journal of Chemistry, 2017, 10, 732738 [129] Gholamhossein Grivani, Sara Husseinzadeh Baghan, Mohammad Vakili, Aliakbar Dehno Khalaji, Vida Tahmasebi, Václav Eigner, Michal Dušek, A new copper(II) Schiff base complex containing asymmetrical tetradentate N2O2 Schiff base ligand: Synthesis, characterization, crystal structure and DFT study, Journal of Molecular Structure, 2015, 1082, 91–96 [130] Ali Hossein Kianfar, Roghayeh Hashemi Fath, Theoretical study of the 154 [131] [132] [133] [134] [135] [136] [137] [138] [139] structures of Schiff base compounds and thermodynamic study of the tautomerism reactions byab initio calculations, Egyptian Journal of Petroleum, 2016 Omima M.I Adly, Ali Taha, Shery A Fahmy, Spectroscopic and structural studies of new mononucleating tetradentate Schiff base metal chelates derived from 5-acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione and 1,3diaminopropane, Journal of Molecular Structure, 2015, 1093, 228–238 S Sobha, R Mahalakshmi, N Raman, Studies on DNA binding behaviour of biologically active transition metal complexes of new tetradentate N2O2 donor Schiff bases: Inhibitory activity against bacteria, Spectrochimica Acta Part A, 2012, 92, 175–183 Kamel Ouari, Sabrina Bendia, Jean Weiss, Corinne Bailly, Spectroscopic, crystal structural and electrochemical studies of zinc(II)-Schiff base complex obtained from 2,3-diaminobenzene and 2-hydroxynaphthaldehyde, Spectrochimica Acta Part A, 2015, 135, 624–631 T Arun, S Packianathan, M Malarvizhi, R Antony, N Raman, Bio-relevant complexes of novel N2O2 type heterocyclic ligand: Synthesis, structural elucidation, biological evaluation and docking studies, Journal of Photochemistry and Photobiology B: Biology, 2015, 149, 93–102 Soraia Meghdadi, Mehdi Amirnasr, Mona Majedi, Maryam Bagheri, Ahmad Amiri, Soheila Abbasi, Kurt Mereiter, Template synthesis, and X-ray crystal structures of copper(II) and nickel(II) complexes of new unsymmetrical tetradentate Schiff base ligands Electrochemistry, antibacterial properties, and metal ion effect on hydrolysis recondensation of the ligand, Inorganica Chimica Acta, 2015, 437, 64–69 Neslihan Beyazit, Berna Catıkkas, Sahin Bayraktar, Cahit Demetgül, Synthesis, characterization and catecholase-like activity of new Schiff base metal complexes derived from visnagin: Theoretical and experimental study, Journal of Molecular Structure, 2016, 1119, 124–132 E Akila, M Usharani, S Ramachandran, P Jayaseelan, G Velraj, R Rajavel, Tetradentate-arm Schiff base derived from the condensation reaction of 3,3’-dihydroxybenzidine, glyoxal/diacetyl and 2-aminophenol: Designing, structural elucidation and properties of their binuclear metal(II) complexes, Arabian Journal of Chemistry, 2017, 10, S2950–S2960 Arun Kumar, Monika Agarwal, Ajai K Singh, R.J Butcher, Palladium(II), platinum(II), ruthenium(II) and mercury(II) complexes of potentially tridentate Schiff base ligands of (E, N, O) type (E=S, Se, Te): Synthesis, crystal structures and applications in Heck and Suzuki coupling reactions Inorganica Chimica Acta 2009, 362, 3208–3218 Takashi Tsuno, Haruka Iwabe, Henri Brunner, Synthesis and structural 155 [140] [141] [142] [143] [144] [145] [146] characterization of isomeric palladium(II) complexes with chiral N,Obidentate ligands, Inorganica Chimica Acta, 2013, 400, 262–266 Amalina Mohd Tajuddin, Bohari M Yamin, El Hassane Anouar, Abdulrahman I Alharthi, Kalavathy Ramasamy, Hadariah Bahron, DFT analysis and bioactivity of 2-((E)-(4methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes, Arabian Journal of Chemistry, 2017, 10, 769–780 Chetan T Prabhakara, Sangamesh A Patil, Shivakumar S Toragalmath, Synthesis, characterization and biological approach of metal chelates of some first row transition metal ions with halogenated bidentate coumarin Schiff bases containing N and O donor atoms, Journal of Photochemistry & Photobiology, B: Biology, 2016, 157, 1–14 H Saleem, S Subashchandrabose, Y Erdogdu, V Thanikachalam, J Jayabharathi, FT-IR, FT-Raman spectral and conformational studies on (E)2-(2-hydroxybenzylidenamino)-3-(1H-indol-3yl) propionic acid, Spectro chimica Acta Part A, 2013, 101, 91–99 Mukesh Choudhary, R.N Patel, S.P Rawat, Synthesis, electrochemical, structural, spectroscopic and biological activities of mixed ligand copper (II) complexes with 2-{[(Z)-(5-bromo-2 hydroxyphenyl)methylidene]amino}benzoic acid and nitrogenous base, Journal of Molecular Structure, 2014, 1060, 197–207 I Mohamed Mustafa, M.A Hapipah, Mahmood Ameen Abdulla, T Robinson Ward, Synthesis, structural characterization, and anti-ulcerogenic activity of schiff base ligands derived from tryptamine and 5-chloro, 5-nitro, 3,5-ditertiarybutyl salicylaldehyde and their nickel(II), copper(II), and zinc(II) complexes, Polyhedron 28, 2009, 3993–3998 Ganesh More, Darshana Raut, K Aruna, Sakina Bootwala, Synthesis, spectroscopic characterization and antimicrobial activity evaluation of new tridentate Schiff bases and their Co(II) complexes, Journal of Saudi Chemical Society 2017 Md Azharul Arafath , Farook Adam , Mohd R Razali , Loiy E Ahmed Hassan , Mohamed B Khadeer Ahamed , Amin Malik S.A Majid, Synthesis, characterization and anticancer studies of Ni(II), Pd(II) and Pt(II) complexes with Schiff base derived from N-methylhydrazinecarbothioamide and 2hydroxy-5-methoxy-3-nitrobenzaldehyde, 2017, 1130, 791–798 156 157