Synthesis, structure and in vitro cytostatic activity study of the novel organotin(IV) derivatives of p-aminobenzenesulfonic acid

Four new p-aminobenzenesulfonate organotin complexes, [(n-Bu3Sn)(O3SC6H3-NH2-4)](n) (1), [(n-Bu2S-n)(4)(O)(2)(OH)(2)(O3SC6H4-NH2-4)(2)] (2), [(Me2Sn)(4)(O)(2)(OH)(2)(O3SC6H4-NH2-4)(2)] (3) and [{(n-BuSn)(12)O-14(O-H) (6)}(O3SC6H4-NH2-4)(2)center dot 3C(4)H(8)O(2)] (4 center dot diox), were synthesized by reaction of p-aminobenzenesulfonic acid with tributyltin oxide, dibutyltin oxide, dimethyltin oxide and monobutyltin oxide, respectively. These complexes were characterized by elemental analysis, FT-IR, NMR (H-1, C-13, Sn-119) spectroscopy as well as single-crystal X-ray diffraction. The crystal structure of complex 1 reveals that it is a 1D zig-zag chain structure and further interlinked into a 2D network by intermolecular interaction (N-H center dot center dot O). The structure analysis indicates that complexes 2 and 3 are the ladder-like structure including three alternate Sn2O2 rings, and further result in the formation of a 3D supramolecular architecture for 2 and a 2D supramolecular network for 3 by extensive hydrogen-bonding interactions (O-H center dot center dot center dot O,N-H center dot center dot center dot O). Complex 4 exhibits a dodecanuclear organooxotin cages, which are connected into a hydrogen-bonded 2D structure. Furthermore, complexes 1-4 were evaluated for their in vitro cytostatic activity against the human lung cancer cells (A549) and the human hepatocellular carcinoma cells (HepG-2). The preliminary screen shows that organotin derivatives with increasing number n-butyl group exhibitsignificantly higher cytostatic activity, and much higher than methyl group. (C) 2018 Elsevier B.V. All rights reserved.