Organotin flufenamates: Synthesis, characterization and antiproliferative activity of organotin flufenamates
摘要:
The organotin flufenamates [Me-2(flu)SnOSn(flu)Me-2](2) (1), [Bu-2(flu)SnOSn(flu)Bu-2](2) (2) and [Bu2Sn(flu)(2)] (3) have been prepared and structurally characterized by means of vibrational and NMR (H-1, C-13 and Sn-119) spectroscopy. The crystal structure of [Me-2(flu)SnOSn(flu)Me-2](2) (1) has been determined by X-ray crystallography. Three distannoxane rings are present to the dimeric tetraorganodistannoxane of planar ladder arrangement. The structure is centro-symmetric and features a central rhombus Sn2O2 unit with two additional tin atoms linked at the O atoms. Six-coordinated tin centers are present in the dimer distannoxane. This structure is self-assembled via pi -> pi and C-H -> pi stacking interactions. Flufenamic acid and flufenamates were evaluated for antiproliferative activity in vitro. Among the compounds tested [Bu-2(flu)SnOSn(flu)Bu-2](2) (2) and [Bu2Sn(flu)(2)] (3) exhibited high cytotoxic activity against the cancer cell line A549 (non-small cell lung carcinoma). (c) 2005 Elsevier B.V. All rights reserved.