Synthesis, characterization and biological activity of diorganotin complexes with ONO terdentate Schiff base

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• 作者：See Mun Lee ; Hapipah Mohd. Ali ; Kae Shin Sim ; Sri Nurestri Abdul Malek ; Kong Mun Lo
• 关键词：Diorganotin ; Schiff base ; Cytotoxic activity
• 刊名：Inorganica Chimica Acta
• 出版年：2013
• 出版时间：1 September, 2013
• 年：2013
• 卷：406
• 期：Complete
• 页码：272-278
• 全文大小：893 K

文摘

Diorganotin(IV) complexes with general formula R₂SnL [H₂L = (E)-N¡ä-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H₂L₁) and (E)-N¡ä-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H₂L₂); R = Me, Bu, Ph, Cy, Bz, o-ClBz and p-ClBz (1-14)] have been synthesized and characterized by IR, ¹H, ¹³C and ¹¹⁹Sn NMR spectroscopic techniques and single crystal X-ray diffractometry. The structure of the complexes, {[1-(5-bromo-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 1, {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 8 and {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dicyclohexyltin(IV), 11 reveals a five-coordinated, trigonal-bipyramidal geometry, whereby the trigonal plane of the complexes consists of the imine nitrogen atom and alkyl groups from the diorganotin moieties. The complexes are stabilized by a strong intramolecular hydrogen bonding between N(2) and O(3)-H(3). The Schiff bases and their corresponding diorganotin(IV) complexes have been evaluated against three human carcinoma cell lines, namely HT29 (human colon carcinoma cell line), SKOV-3 (human ovarian cancer cell line) and MCF7 (hormone-dependent breast carcinoma cell line), for their cytotoxic activities. The dimethyltin derivatives and dibutyltin derivatives of the Schiff base ligands display good cytotoxic activities against the tested cell lines.