Room temperature synthesis and antibacterial activity of new sulfonamides containing n,n-diethyl-substituted amido moieties

Int J Med Chem. 2012;2012:367815. doi: 10.1155/2012/367815. Epub 2012 Oct 17.

Abstract

Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities. We have synthesized a series of α-tolylsulfonamide, 1-11 and their substituted N,N-diethyl-2-(phenylmethylsulfonamido) alkanamide derivatives, 12-22 in improved and excellent yields in aqueous medium at room temperature through highly economical synthetic routes. The chemical structures of the synthesized compounds 1-22 were confirmed by analytical and spectral data such as IR, (1)H- and (13)C-NMR, and mass spectra. The in vitro antibacterial activity of these compounds along with standard clinical reference, streptomycin, was investigated on two key targeted organisms. It was observed that 1-(benzylsulfonyl)pyrrolidine-2-carboxylic acid, 2 emerged as the most active compound against Staphylococcus aureus at MIC value of 1.8 μg/mL while 4-(3-(diethylamino)-3-oxo-2-(phenylmethylsulfonamido) propyl)phenyl phenylmethanesulfonate, 22 was the most active sulfonamide scaffold on Escherichia coli at MIC value of 12.5 μg/mL.