Synthesis, Characterization and Antitumour Activities of Di-n-Butyl- and Dimethyltin D-(+)-Camphorates

The synthesis and characterization di-n-butyland dimethyltin D-(+)-camphorates, respectively compounds 1 and 2, are reported. Compound 1 displays antitumoural activity in vitro, and is more active than cisplatin, 5-fluorouracil and etoposide against seven tumoural cell lines of human origin, but less active than methotrexate and doxorubucin. Several diorganotin derivatives of dicarboxylic acids are active in vitro against human tumoural cell lines1-6. Nevertheless, diorganotin derivatives of dicarboxylic acids with proven antitumour activity in vitro remain rather rare. The present paper reports the synthesis and characterization of two novel diorganotin dicarboxylates, di-n-butyland dimethyltin D-(+)-camphorates, in order to further investigate the influence of the structure of such a dicarboxylate moiety on antitumour properties7. The antitumour activity of the di-n-butyltin compound is presented, that of the dimethyltin compound being provided for comparison. Di-n-butyland dimethyltin D-(+)-camphorates, respectively compounds 1 and 2, were prepared by condensing the appropriate diorganotin oxide with camphoric acid in refluxing toluene/ethanol 4/1 under elimination of the azeotrope water/toluene/ethanol81. They were recrystallized from ethanol/petroleum ether, m.p. 138-140 C, yield" 90%, and methylene chloride/hexane, m.p. 258259 C, yield: 96%, respectively. The MSssbauer parameters of compounds 1 and 2 are respectively I.S." 1.39, Q.S.’ 3.32, ]-’1: 1.06, 1"2:0.92 and I.S." 1.35, Q.S" 3.89, FI" 0.93, F2" 1.02 mm/s. H and 3CNMR data are presented in Table1.