Synthesis, Characterization and biological evaluation of chiral pyrrolidine sulphonamide mannich bases from tartaric acid

A series of novel chiral 3,4-disubstituted pyrrolidine sulphonamides containing imidazole mannich bases N,N'- ((3S,4S)-1-(2-(2-((4-chloro-2-methyl-1- (piperidin/morpholino/(4-methyl piperazin)-1-yl methyl)-1H-imidazol-5- yl)methylene)hydrazinyl)-2-oxoethyl)pyrrolidine -3,4-diyl)bis ((thiophene-2)/(1-methyl-1H-imidazole-4-)/(4-nitro benzene)sulphonamide) (16a-16i) were synthesized in stereoselective route starting from L-(+) tartaric acid . At the out set, L-(+) tartaric acid was converted into pyrrolidine sulphonamide derivatives N,N'-((3S,4S)-1-(2-hydrazinyl- 2-oxoethyl)pyrrolidine-3,4-diyl)bis ((thiophene-2-)/(1-methyl-1H-imidazole-4-)/(4-nitro benzene) sulphonamide) (12a-12c) by following systematic synthetic procedure depicted in the schemes. The intermediates (12a-12c) were condensed with 4-chloro-2-methyl-1-(piperidin/morpholino/(4-methylpiperazin)-1-ylmethyl)-1H-imidazole-5- carbaldehyde (15 a-15c) to afford the title compounds N,N'-((3S,4S)-1-(2-(2-((4-chloro-2-methyl-1-(piperidin /morpholino/(4-methylpiperazin)-1-ylmethyl)-1H-imidazol-5-yl)methylene) hydrazinyl)-2-oxoethyl) pyrrolidine-3,4- diyl)bis((thiophene-2)/(1-methyl-1H-Imidazole-4-)/(4-nitrobenzene) sulphonamide) (16a-i). The structure of the newly synthesized compounds were characterized by 1HNMR, C13NMR, Mass, IR and elemental analysis. The prepared compounds have been screened for their antibacterial and antifungal activities

Author(s): B. Santosh Kumar1, P. Raveendra Reddy1, G. Madhu2, L. K. Ravidranath1

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