Triphenyltin derivatives of sulfanylcarboxylic esters

The reaction of 3-(aryl)-2-sulfanylpropenoic acids [H2xspa; x: p=3-phenyl-, f=3-(2-furyl)-, t=3-(2-thienyl)-] with methanol or ethanol gave the corresponding methyl (Hxspme) or ethyl (Hxspee) esters. The reaction of these esters (HL) with triphenyltin(IV) hydroxide gave compounds of the type [SnPh3L], which were isolated and characterized as solids by elemental analysis, IR spectroscopy and mass spectrometry and in solution by multinuclear (1H, 13C and 119Sn) NMR spectroscopy. The structures of [SnPh3(pspme)], [SnPh3(fspme)] and [SnPh3(fspee)] were determined by X-ray diffractometry and the antimicrobial activity against E. coli, S. aureus, B. subtilis, P. aeruginosa, Resistant P. aeruginosa (a strain resistant to ‘carbapenem’), and C. albicans was tested and the in vitro cytotoxic activity against the HeLa-229, A2780 and A2780cis cell lines was determined for all compounds. The characteristics of compounds formed by sulfanylcarboxylic esters and triphenyltin(IV) have been explored both in solid state and in solution. Their antibacterial activities and the in vitro cytotoxic activities against the HeLa-229, A2780 and A2780cis cell lines are discussed. [Display omitted] •Synthesis of new triphenyltin(IV) compounds using esters of sulfanylcarboxylic acids•Antimicrobial activity•Cytotoxic activity against cancer cell lines•Esterification and substituent influences on structure and biological activity