Synthesis of tri-n-butyltin taurocholate, taurodeoxycholate and glycocholate

The bile acids, taurocholic, taurodeoxycholic and glycocholic acid, were reacted with bis(tri‐n‐butyltin) oxide (TBTO) to form 1:1 derivatives. The water of reaction was removed with 2, 2‐dimethoxypropane or by azeotropic distillation with benzene. The compounds were characterized by 13C and 119Sn NMR, IR, elemental analysis, molecular weight determination, DTA, TGA, and conductance measurements. The data indicated that tri‐n‐butyltin glycocholate forms a covalent ester, tin being tetracoordinated. The taurocholic and taurodeoxycholic acid derivatives contain one molecule of coordinated water. They partially dissociate in polar solvents. The taurocholic and glycocholic acid derivatives were tested in vitro as anticancer agents and exhibited ED50 in the 0.2–0.4 ppm (mg kg−1) range against KB epidermoid tumor and P‐388 leukemia using NCI protocols.