Synthesis, characterization, and antibacterial activity of dithiophosphonates and amidodithiophosphonates

Abstract

New dithiophosphonates [RPS2(OR1)]- (R1 = fenchyl and bornyl) and amidodithiophosphonates [RPS2(NHR2)]- (R2 = 2-benzyloxycyclohexyl and 1-(4-fluorophenyl)ethyl) have been synthesized by the reaction of (ArPS2)2 (Ar = p-MeO-C6H4) and (1R)-endo-(+)-fenchyl alcohol and (-)-borneol or the amines (1S,2S)-(+)-2-benzyloxycyclohexylamine and (R)- (+)-1-(4-fluorophenyl)ethylamine in toluene. All compounds have been characterized by elemental analyses, IR, NMR (1H, 13C, and 31P) spectroscopy as well as MS measurements. [tBuNH3][(CH3OC6H4)P(OR)S2] (R = bornyl) (2) was structurally characterized by X-ray crystallography. The antibacterial activity of the dithiophosphonates has been investigated on seven gram-positive, seven gram-negative bacteria, and three different Methicillin-Resistant Staphylococcus aureus (MRSA) strains. Compound 1 exhibited the most potent anti-MRSA activity, whereas compound 2 and 4 showed weak anti-MRSA activity. Copyright © 2015 Taylor & Francis Group, LLC.