Comparative study of the antibacterial activity of N,N-diethylamido substituted p-toluenesulfonamides to their α-toluenesulfonamide counterparts.
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Asian Network of Scientific information
Abstract
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Reaction of p-toluenesulfonyl chloride with amino acids gave sulfonamides
p-T1a-k which upon amidation afforded p-T2a-k. Similarly, treatment involving
α-toluenesulfonyl chloride and amino acids afforded the sulfonamides α-T1a-k.
These two classes of sulfonamides were synthetically modified at their COOH end
position to achieve N,N-diethylamido substituted p-toluenesulfonamides p-T2a-k
and α-toluenesulfonamides α-T2a-k, respectively. The chemical structures of the
compounds were validated with IR, Mass spectra, NMR as well as elemental
analytical data. Both classes of compounds were screened against Escherichia coli
and Staphylococcus aureus and their activity were compared. It was remarkable
to note that the α-toluene sulfonamides α-T2a-k were more active than their
p-toluenesulfonamide counterparts p-T2a-k. Compound 1-(benzylsulfonyl)-N,Ndiethylpyrrolidine-
2-carboxamide α-T2a was the most potent antibacterial
compound on S. aureus with MIC value of 3.12 μg mLG1 while N,N-Diethyl-3-
phenyl-2-(phenylmethylsulfonamide) propanamide α-T2j emerged as the best
antibacterial motif against E. coli with MIC value of 12.5 μg mLG1. Hence, these
compounds especially the α-toluenesulfonamide core structural templates are good
candidates for further study for future drug discovery.
Keywords
QD Chemistry