Synthesis and Characterization of O,S-Dimethylphosphoramidothioate and N-Acetyl O,S-Dimethylphosphoramidothioate

Abstract

O,S-Dimethylphosphoramidothioate (methamidophos) and N-acetyl O,S-dimethylphos- phoramidothioate (acephate) were synthesized by new methods to investigate the structure–activity study of acetyl cholinesterase (AChE) inhibition through the parameters of logP, δ 31P, and IC50. After their characterization by NMR (31P, 31P{ 1H}, 13C, and 1H), IR, and mass spectroscopy, logP and δ 31P (31P chemical shift in NMR) were used to evaluate lipophilicity and electronical properties. The logP values for methamidophos and acephate were experimentally determined by the GC-shake-flask method, and the ability of the compounds to inhibit human AChE was evaluated by a modified Ellman's assay. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.