Synthesis, characterization and antimicrobial activity of novel mannich bases of indol derivatives

New novel derivatives of 2-(5-chloro-3-(4-substituted phenylimino)methyl)-1-(pyridine-4-yl)-1H-pyrazol-3-yl)-1Hindol- 1-yl)-N1-(2-oxo-1-(4-substituted piperidin-1-ylmethyl)indolin-3-ylidene) acetohydrazide 9(a-o) were prepared by the (mannich reaction) condensation of 2-(5-chloro-3-(4-substituted phenylimino)methyl)-1-(pyridin-4-yl)-1Hpyrazol- 3-yl)-1H-indol-1-yl)N1-(2-oxoindolin-3-ylidene)acetohydrazide 8(a-e) with piper dine/morpholine/Nmethyl piperizine and formaldehyde in DMF. The compounds 8(a-e) were obtained by the reaction of 2-(5-chloro-3- (4-substituted phenylimino)methyl)-1-(pyridin-4-yl)-1H-pyrazol-3-yl) 1H-indol-1-yl)acetohydrazaide 7(a-e) with isatin. Subsequently 7(a-e) were obtained by the reaction of ethyl-2-(5-chloro-3-(4-substituted phenylimino)methyl)- 1-(pyridin-4-yl) -1H-pyrazol-3-yl)-1H-indol-1-yl)acetate 6(a-e) with hydrazine hydrate. The synthon 6(a-e) were obtained by the reaction of ethyl-2-(5-cloro-3-(4-formyl-1-(pyridine-4-yl)-1H-pyrazol-3-yl)-1H-indol-1-yl)acetate(5) with 4-substituted anilines. The compound (5) was obtained by the Vilsmeier-Haack reaction of 2-(5-chloro-3-(1- (2-pyridin-4-yl)hydrazono)ethyl)-1H-indol-1-yl)acetate (4) at 0-50C. The 2-(5-chloro-3-(1-(2-pyridin-4- yl)hydrazono)ethyl)-1H-indol-1-yl)acetate (4) was obtained by reaction of 1-(5-chloro-1H-indol-3-yl)ethanone (1) with chloro ethyl acetate in K2CO3 and DMF, the product obtained in the reaction is further treated with 4- hydrazino pyridine. Finally the title of the compounds 9(a-o) were subjected to antimicrobial studies and incorporated in the present studies. All the compounds were characterized by spectral studies (IR, 1H-NMR, 13CNMR, Mass) and Elemental analysis.

Author(s): J. Sreeramulu, P. Ashokgajapathiraju, K. Venugopal, L. K. Ravindranath and S. Muralikrishna

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