Synthesis, structural characterization and cytotoxic activity of diorganotin(IV) complexes ofN-(5-halosalicylidene)-α-amino acid

Abstract

Fourteen new diorganotin(IV) complexes of N-(5-halosalicylidene)-α-amino acid, R′2Sn(5-X-2-OC6H3CHNCHRCOO) (where X = Cl, Br; R = H, Me, i-Pr; R′ = n-Bu, Ph, Cy), were synthesized by the reactions of diorganotin halides with potassium salt of N-(5-halosalicylidene)-α-amino acid and characterized by elemental analysis, IR and NMR (1H, 13C and 119Sn) spectra. The crystal structures of Bu2Sn(5-Cl-2-OC6H3CHNCH(i-Pr)COO) and Ph2Sn(5-Br-2-OC6H3CHNCH(i-Pr)COO) were determined by X-ray single-crystal diffraction and showed that the tin atoms are in a distorted trigonal bipyramidal geometry and form five- and six-membered chelate rings with the tridentate ligand. Bioassay results of a few compounds indicated that the compounds have strong cytotoxic activity against three human tumour cell lines, i.e. HeLa, CoLo205 and MCF-7, and the activity decreased in the order Cy>n-Bu>Ph for the R′ group bound to tin. Copyright © 2005 John Wiley & Sons, Ltd.