Preparation and antimicrobial studies of acyclic sulfamates

A series of acyclic sulfamates have been prepared and tested for antimicrob ial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methox yphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoro ethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. T reatment of lad with glycidol gave the glycidyl carbamates 2a-d. Internal c yclisation afforded the corresponding 3-hydroxymethyl-2-oxazolidinones 3a d , which in turn were hydrolysed to give the free amino alcohols 4a-d. The y ields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a d, 4a d indicated 2a-d and 3e to be possible antimicrobial agents. A mor e thorough analysis of these compounds revealed a minimum inhibition concen tration (MIC) of 128 and 64 mg 1(-1) for glycidyl p-methoxyphenoxysulfonylc arbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, agai nst Branhamella catarrhalis.