Synthesis, Crystal Structure, Thermal Stability and Anti-tumor Activity In Vitro of Bis(tricyclohexyltin) Pimelicarboxylate
朱小明;邝代治;冯泳兰;张复兴;庾江喜;蒋伍玖;张志坚
a(Department of Chemistry and Material Science, Hengyang Normal University; Key Laboratory of Functional Organometallic Materials of Hengyang Normal University, College of Hunan Province, Hengyang 421008, Hunan)
b(Department of Life Science, Hengyang Normal University, Hengyang 421008, Hunan)
Synthesis, Crystal Structure, Thermal Stability and Anti-tumor Activity In Vitro of Bis(tricyclohexyltin) Pimelicarboxylate
a(Department of Chemistry and Material Science, Hengyang Normal University; Key Laboratory of Functional Organometallic Materials of Hengyang
Normal University, College of Hunan Province, Hengyang 421008, Hunan)
b(Department of Life Science, Hengyang Normal University, Hengyang 421008, Hunan)
Bis(tricyclohexyltin) pimelicarboxylate, [(CH2)5(CO2SnCy3)2] (1), has been synthesized by the reaction of tricyclohexyltin hydroxide with pimelic acid and characterized by means of IR, 1H and 13C NMR, elemental analysis and X-ray diffraction. Complex 1 crystallizes in triclinic space group P with a = 11.569(3), b = 12.0419(2), c = 17.3988(4) Å, α = 81.4310(10), = 79.8270(10), γ = 69.7060(10)º, V = 2227.60(9) Å3, Z = 2, C43H76O4Sn2, Mr = 894.42, Dc = 1.333 g·cm-3, = 1.157 mm-1, F(000) = 932, GOOF = 1.339, the final R = 0.0452 and wR = 0.1333 for 6709 observed reflections (I > 2(I)). Complex 1 shows discrete dimeric structures and the tin atoms have a distorted tetrahedral geometry. The 1D chain structure of complex 1 is formed by intermolecular Sn···O interactions. Complex 1 displays good thermal stability under 553 K and has selective antibacterial property. Complex 1 is strong in vitro anti-tumor activity against five human tumor cell lines, Colo205, HepG2, MCF-7, Hela and NCI-H460, and is significantly higher than that in the clinical use of carboplatin.
Bis(tricyclohexyltin) pimelicarboxylate, [(CH2)5(CO2SnCy3)2] (1), has been synthesized by the reaction of tricyclohexyltin hydroxide with pimelic acid and characterized by means of IR, 1H and 13C NMR, elemental analysis and X-ray diffraction. Complex 1 crystallizes in triclinic space group P with a = 11.569(3), b = 12.0419(2), c = 17.3988(4) Å, α = 81.4310(10), = 79.8270(10), γ = 69.7060(10)º, V = 2227.60(9) Å3, Z = 2, C43H76O4Sn2, Mr = 894.42, Dc = 1.333 g·cm-3, = 1.157 mm-1, F(000) = 932, GOOF = 1.339, the final R = 0.0452 and wR = 0.1333 for 6709 observed reflections (I > 2(I)). Complex 1 shows discrete dimeric structures and the tin atoms have a distorted tetrahedral geometry. The 1D chain structure of complex 1 is formed by intermolecular Sn···O interactions. Complex 1 displays good thermal stability under 553 K and has selective antibacterial property. Complex 1 is strong in vitro anti-tumor activity against five human tumor cell lines, Colo205, HepG2, MCF-7, Hela and NCI-H460, and is significantly higher than that in the clinical use of carboplatin.
基金资助: Supported by the Natural Science Foundation of Hunan Province (No.13JJ3112), Scientific & Technological Projects of Hunan Province (Nos. 2013TZ2025, 2014NK3086, 2014FJ3060), the Open Fund Project of Key Laboratory of Functional Organometallic Materials of Hengyang Normal University (Nos. 13K105, 14K014, 13K01-05, GN14K01), Aid Programs for Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province, the Key Discipline of Hunan Province, the Scientific Research Fund of Hunan Provincial Education Department of China (No. 15C0199, 15C0200, 14C0171, 14C0168) and the Science Foundation of Hengyang Normal University of China (No. 12C45)
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引用本文:
朱小明;邝代治;冯泳兰;张复兴;庾江喜;蒋伍玖;张志坚. Synthesis, Crystal Structure, Thermal Stability and Anti-tumor Activity In Vitro of Bis(tricyclohexyltin) Pimelicarboxylate[J]. 结构化学, 2015, 34(11): 1652-1658.
ZHU Xiao-Ming;KUANG Dai-Zhi; FENG Yong-Lan ZHANG Fu-Xing;U Jiang-Xia JIANG Wu-Jiu;ZHANG Zhi-Jian. Synthesis, Crystal Structure, Thermal Stability and Anti-tumor Activity In Vitro of Bis(tricyclohexyltin) Pimelicarboxylate. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2015, 34(11): 1652-1658.
REFERENCES
(1)Yu, J. X.; Kuang, D. Z.; Feng, Y. L.; Zhu, X. M.; Jiang, W. J.; Zhang, F. X. Solvothermal syntheses, crystal structures, thermal stability and quantum chemistry of dinuclear trialkyltin complexes constructed by camphoric acid. Chin. J. Struct. Chem. 2014, 33, 1521–1526.
(2)Wang, J. Q.; Kuang, D. Z.; Zeng, R. Y.; Zhang, F. X.; Feng, Y. L.; Chen, Z. M. Synthesis, crystal structure and quantum chemistry study of tri(o-bromobenzyl)tin ferrocenecarboxylate. Chin. J. Struct. Chem. 2007, 26, 674–678.
(3)Zhang, Z. J.; Kuang, D. Z.; Feng, Y. L.; Zhu, X. M.; Yu, J. X.; Jiang, W. J. Synthesis, structure and acaricidal activity of tricyclohexyltin benzoate. Chin. J. Struct. Chem. 2014, 33, 1287–1292.
(4)Hong, M.; Yin, H. D.; Zhang, X. Y.; Li, C.; Yue, C. H.; Cheng, S. Di- and tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: synthesis, characterization and in vitro antitumor activities. J. Organomet. Chem. 2013, 724, 23–31.
(5)Anjorin, C.; Song, X.; Kumar, D.; Pike, R.; Dios, A. D.; Eng, G. Crystal structures of two polymeric bis(triphenyltin) malonates. J. Coord. Chem. 2010, 63, 4031–4040.
(6)Ng, S. W.; Kumar, D. V. G.; Li, S. L.; Mark, T. C. W. µ-Oxalatobis(tricyclohexyltin), a dinuclear tin compound with isomeric pentacoordinate tin sites. J. Organomet. Chem. 1994, 467, 47–49.
(7)Cao, H.; Li, D. L.; Yu, Y.; Tian, L. J. Synthesis, crystal structure and anti-bacterial activity of bis(trcyclohexyltin) succinate. J. Jinggangshan University (Nat. Sci.) 2012, 33, 30–33.
(8)Xie, Q. L.; He, X. L.; He, S. J.; Su, G. X. Synthesis characterization and pesticidal activities of bis(trialkyltin) dicarboxylates. Acta Chim. Sinica 1999, 57, 210–218.
(9)Jan, C.; Karel, H.; Ivana, C.; Robert, J.; Jiŕí, B.; Antonín, L.; Aleš, R.; Jarosalav, H. Structural study of bis(triorganotin(IV)) esters of 4-ketopimelic acid. J. Organomet. Chem. 2006, 691, 2631–2640.
(10)Kuang, D. Z.; Feng, Y. L.; Yu, J. X.; Zhang, F. X.; Jiang, W. J.; Peng, Y.; Zhu, X. M.; Tan, Y. X. Microwave assisted solid-state synthesis, crystal structure, properties of the coordination polymer constructed from tricyclohexyltin hydroxide and o-ferrocenylcarbonyl benzoic acid. Chem. J. Chin. Univ. 2014, 35, 1629–1634.
(11)Lei, B.; Jia, Y. G.; Liu, L. Y.; Chang, W. X.; Li, J. Synthesis and crystal structure of novel Sn–O clusters generated from nBu2SnO and esters. Chin. J. Struct. Chem. 2010, 29, 1373–1379.
(12)Chandrasekhar, V.; Thirumoorthi, R.; Metre, R. K.; Mahanti, B. Steric control in the reactions of 3-pyrazolecarboxylic acid with diorganotin dichlorides. J. Organomet. Chem. 2011, 696, 600–606.
(13)Zhang, F. X.; Kuang, D. Z.; Feng, Y. L.; Wang, J. Q.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Synthesis, structure and antitumor activity of tri(o-bromobenzyl) tin dithiotetrahydropyrrolocarbamate. Chin. J. Appl. Chem. 2014, 31, 285–289.
(14)Adama, M. S.; Du, D. F.; Zhu, D. S.; Xu, L. The one-dimensional chain: synthesis, crystal structure and biological activities of tricyclohexyl tin carboxylates. Chin. J. Inorg. Chem. 2011, 27, 107–113.
(15)Yin, H. D.; Wang, C. H.; Hong, M. Synthesis, properties and crystal structure of diorganotin(Ⅳ) compound with Schiff base ligand pyruvic acid isonicotinyl hydrazone [Ph2Sn(C9H7N3O3)(H2O)]2. Chin. J. Appl. Chem. 2007, 24, 1124–1127.
(16)Yan, W. H.; Kang, W. L.; Li, J. H. Synthesis, crystal structure and antibacterial activity of di-n-butyltin carboxylate. Chemistry 2007, 313–316.
(17)George, M. S. SHELXTL-97: Program for Crystal Structure Analysis. Göttingen. University of Göttingen 1997.
(18)Weng, S. F. Fourier Translation Infrared Spectroscopy Analysis. The second edition. Beijing: Chemical Industry Press 2005, 309–310/326–327.
(19)Tian, L. J.; Cao, H.; Wang, S. X.; Sun, Y. X.; Liu, Z. Synthesis, characterization and cytotoxic activity of tricyclohexyltin(IV) carboxylates derived from cyclic dicarboxylic anhydrides. J. Coord. Chem. 2013, 66, 624–637.
(20)Yin, H. D.; Cui, J. C.; Li, J. Synthesis and crystal structure of organotin compound tirmeyltin(IV) quinoline-2-carboxylate. J. Liaocheng University (Nat. Sci.) 2009, 22, 66–68.
(21)Liu, C. L.; Xu, D.; Wen, Q.; Wang, H. X.; Xie, M. S.; Zhu, D. S. Synthesis, characterizations and thermal stability of a tricyclohexyltin carboxylate based on substituted isophthalic acid. Chemistry 2014, 77, 819–822.
(22)Zhang, Z. J.; Kuang, D. Z.; Zhang, F. X.; Yu, J. X.; Jiang, W. J. Synthesis, crystal structure and biological activities of the tris(2-methyl-2-phenyl)propyl tin trichloroacetic acid ester. Chin. J. Appl. Chem. 2014, 31, 1058–1062.
(23)Wang, Y. H.; Du, X. G.; Wu, X. Y.; Zhu, C. G.; Du, D. F.; Zhu, D. S. Synthesis, crystal structure and biological activities of the novel dinacrocyclic di-n-butyltin carboxylates. Chem. J. Chin. Univ. 2008, 9, 1781–1785.
(24)Yu, J. X.; Feng, Y. L.; Kuang, D. Z.; Zhang, F. X.; Jiang, W. J.; Zhu, X. M. Synthesis, crystal structure, thermal stability and anti-tumor activity in vitro of two tricyclohexyltin aromatic carboxylates. Chin. J. Inorg. Chem. 2014, 30, 1267–1272.
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