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Organotin flufenamates: Synthesis, characterization and antiproliferative activity of organotin flufenamates |
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| Authors: | Dimitra Kovala-Demertzi Vaso N. Dokorou Adam Opolski Maria Zervou |
| Affiliation: | a Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece b Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2110, USA c Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Weigla 12, 53-114 Wroclaw, Poland d National Hellenic Research Foundation, Institute of Organic and Pharmaceutical Chemistry, Vas. Constantinou 48, 11635 Athens, Greece |
| Abstract: | The organotin flufenamates [Me2(flu)SnOSn(flu)Me2]2 (1), [Bu2(flu)SnOSn(flu)Bu2]2 (2) and [Bu2Sn(flu)2] (3) have been prepared and structurally characterized by means of vibrational and NMR (1H, 13C and 119Sn) spectroscopy. The crystal structure of [Me2(flu)SnOSn(flu)Me2]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 π → π and C-H → π stacking interactions. Flufenamic acid and flufenamates were evaluated for antiproliferative activity in vitro. Among the compounds tested [Bu2(flu)SnOSn(flu)Bu2]2 (2) and [Bu2Sn(flu)2] (3) exhibited high cytotoxic activity against the cancer cell line A549 (non-small cell lung carcinoma). |
| Keywords: | Flufenamic acid Diorganotin flufenamates Crystal structure Spectroscopic studies Antitumor agents |
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