Synthesis and characterization ol the new ambidentate O-cholesteryl-O-phenyl phosphorothioate ligand and its organoarsenic derivatives of phenoxarsin-10-yl and phenothiarsin-10-yl phosphorothioate

A new anionic phosphorothioate ligand that incorporates the bioactive chole steryl group was obtained (2), Na(RR'P(S)O; R, O-phenyl; R', O-cholesteryl) from the phenylphosphoramidate (1) and NaH in dioxane. In order to test th e coordination ability of 2, two organoarsenic derivatives were prepared O( C6H4)(2)AsS(O)PRR' (3) and S(C6H4)(2)AsS(O)PRR' (4) by reacting 2 with 10-c hlorophenoxarsine or 10-chlorophenothiarsine. Compounds 2, 3, and 4 were ch aracterized by elemental microanalysis, IR, multielement NMR (H-1, C-13, an d P-31), and mass spectrometry. The spectroscopic data suggest that the lig and is bonded to the arsenic only through the sulfur donor atom in both org anoarsenic derivatives. (C) 2000 John Wiley & Sons, Inc.