Cyclic N-2-Chloroethyl-sulfamide Compounds with a Phosphonate Moiety: Synthesis, Characterization, X-Ray Crystallographic Study and Antimicrobial Evaluation

摘要

An efficient access to a novel series of organophosphorus compounds with a cyclosulfamide moiety is described. Starting from α-hydroxyphosphonates, the 2-chloroethyl-(1, 2, 5- thia- diazoline-2-carbonyloxy-1- dioxide) phosphonates compounds were prepared in three steps including an Abramov reaction, carbamoylation-sulfamoylation with chlorosulfonyl isocyanate and an intramolecular cyclisation. The spectroscopic methods ( 1 H NMR, 13 C NMR, 31 P NMR, MS and IR) were used to determine the structural characteristics of the synthesized compounds and X-ray crystallographic data were provided for compound 3c. Some selected compounds were screened in vitro for their antimicrobial activity against a panel of microorganisms, resulting in a good antibacterial activity compared to standard drugs.