Synthesis and antitumor activity of novel dibutyltin carboxylates of aminoglucosyl derivatives.

In this study, di-n-butyltin(IV) oxide was reacted with the amino glucose analog, cis-4-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl)imido]-4-oxo-2-butenoic acid (1a) and o-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl) carbamoyl] benzoic acid (2a) to give the complexes bis-{cis-4-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl)imido-4-oxo-2-butenoic acid]-di-n-butyltin} carboxylate (1) and bis-{o-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl) carbamoyl-benzoic acid]-di-n-butyltin}carboxylate (2). These two compounds were then characterized by IR, NMR and MS. In vitro tests showed that both compounds have high cytotoxicity in four tumor cell lines (P388, HL-60, A549 and BEL-7402). Clonogenic assays demonstrated that both compounds 1 and 2 have hematopoietic cell toxicity at 10(-6) M.