Synthesis, characterization, and cytotoxic activity of triphenyltin complexes of N-(5-bromosalicylidene)-α-amino acids

被引:20
作者
Yao, Yanze [1 ]
Yang, Min [2 ]
Zheng, Xiaoliang [3 ]
Tian, Laijin [1 ]
机构
[1] Qufu Normal Univ, Key Lab Nat Prod & Pharmaceut Intermediates, Qufu 273165, Peoples R China
[2] Dezhou Univ, Dept Chem, Dezhou 253023, Peoples R China
[3] Zhejiang Acad Med Sci, Inst Mat Med, Hangzhou 310013, Zhejiang, Peoples R China
关键词
alpha-amino acid; crystal structure; cytotoxic activity; organotin complex; Schiff base; STRUCTURAL-CHARACTERIZATION; DIORGANOTIN(IV) COMPLEXES; BIOLOGICAL-ACTIVITY; ANTITUMOR-ACTIVITY; IN-VITRO; X-RAY; CARBOXYLATES; DERIVATIVES;
D O I
10.1515/mgmc-2017-0015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Five new triphenyltin complexes of N-(5-bromosalicylidene)-alpha- amino acids, 5-Br-2- HOC6H3C(H)= NCH(R) COOSnPh3 (where R=H, 1; Me, 2; i-Pr, 3; i-Bu, 4; s-Bu, 5), were synthesized by one-step reactions of triphenyltin hydroxide, 5-bromosalicylaldehyde, and alpha-amino acid in 1:1:1 molar ratios and characterized by elemental analysis, IR, and NMR (H-1, C-13, and Sn-119) spectra. The crystal structures of 5-Br-2- HOC6H3C(H) = NCH(i-Pr) COOSnPh3 (3) and 5-Br-2- HOC6H3C(H) = NCH(s-Bu) COOSnPh3 (5) were determined and showed that the tin atom is five-coordinated and adopts a polymeric trans-O2SnC3 trigonal bipyramidal configuration with the axial positions occupied by a carboxylate oxygen from the ligand and the phenolic oxygen of the ligand in an adjacent complex. Bioassay results indicated that these compounds have stronger cytotoxic activity against three human tumor cell lines, HeLa, CoLo205 and MCF-7, than that of cis-platin used clinically.
引用
收藏
页码:93 / 99
页数:7
相关论文
共 31 条
  • [21] Tian LJ, 2016, CHINESE J STRUC CHEM, V35, P849, DOI 10.14102/j.cnki.0254-5861.2011-1058
  • [22] Synthesis, structure and in vitro cytotoxic activity of two organotin complexes of 2-phenyl-1,2,3-triazole-4-carboxylic acid
    Tian, Laijin
    Kong, Lingdong
    Zhang, Changfa
    [J]. MAIN GROUP METAL CHEMISTRY, 2015, 38 (3-4) : 83 - 91
  • [23] Synthesis, characterization, and cytotoxic activity of tricyclohexyltin(IV) carboxylates derived from cyclic dicarboxylic anhydrides
    Tian, Laijin
    Cao, Hui
    Wang, Shouxin
    Sun, Yuxi
    Liu, Zhi
    [J]. JOURNAL OF COORDINATION CHEMISTRY, 2013, 66 (04) : 624 - 637
  • [24] Synthesis, characterization and cytotoxic activity of new diorganotin(IV) complexes of N-(3,5-dibromosalicylidene)tryptophane
    Tian, Laijin
    Liu, Xicheng
    Zheng, Xiaoliang
    Sun, Yuxi
    Yan, Dongmei
    Tu, Linglan
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2011, 25 (04) : 298 - 304
  • [25] Synthesis, structural characterization and cytotoxic activity of diorganotin(IV) complexes of N-(5-halosalicylidene)tryptophane
    Tian, Laijin
    Yang, Hongjun
    Zheng, Xiaoliang
    Ni, Zhonghai
    Yan, Dongmei
    Tu, Linglan
    Jiang, Jianzhuang
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (01) : 24 - 31
  • [26] Tian LJ, 2006, APPL ORGANOMET CHEM, V20, P74, DOI 10.1002/aoc.1005
  • [27] Synthesis, characterization and biological activity of triorganotin 2-phenyl-1,2,3-triazole-4-carboxylates
    Tian, LJ
    Sun, YX
    Li, HJ
    Zheng, XL
    Cheng, YZ
    Liu, XL
    Qian, BH
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (08) : 1646 - 1652
  • [28] Synthesis, structural characterization and cytotoxic activity of diorganotin(IV) complexes of N-(5-halosalicylidene)-α-amino acid
    Tian, LJ
    Qian, BC
    Sun, YX
    Zheng, XL
    Yang, M
    Li, HJ
    Liu, XL
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (08) : 980 - 987
  • [29] Tiekink E.R. T., 1994, TRENDS ORGANOMET CHE, V1, P71
  • [30] Synthesis, characterization, biocide and toxicological activities of di-n-butyl- and diphenyl-tinIV-salicyliden-β-amino alcohol derivatives
    Zamudio-Rivera, LS
    George-Tellez, R
    López-Mendoza, G
    Morales-Pacheco, A
    Flores, E
    Höpfl, H
    Barba, V
    Fernández, FJ
    Cabirol, N
    Beltrán, HI
    [J]. INORGANIC CHEMISTRY, 2005, 44 (15) : 5370 - 5378