Synthesis Characterization and Biological Evaluation of 2-(3-(2-Chloro-3-Oxo-4-Phenylcyclobutyl)-1h-Indol-1-Yl)-N'-(Thiazol-2-Yl) Acetohydrazide

Author(s): S. Muralikrishna, L. K. Ravindranath, S. Chandra Kala and S. Arun Kumar

This article is aimed to synthesize, characterize and biological activity of a series of synthesis of 2-(3-(2-chloro-3- oxo-4-phenylcyclobutyl)-1H-indol-1-yl)-N'-(thiazol-2-yl) acetohydrazide 4(a-f). Indole-3-carbaldehyde and chloro ethyl acetate were dissolved in DMF. To this reaction mixture, anhydrous K2CO3 was added and the reaction mixture was stirred at room temperature (35oC) for 8 hrs. To afford 2-(3-formyl-1H-indol-1-yl)acetate. To this reaction mixture added aniline, EtOH and three drops of acetic acid is added and then heated on a steam bath for 5-6 hrs. Compound (A) Ethyl 2-(3-phenyl imino)methyl-1H-Indole-1-yl-acetate was obtained. Compound (A) is converted into ethyl 2-(3-(2-chloro-3-oxo-4- phenylcyclobutyl)-1H-indol-1-yl)acetate (1) by using of conditions (1) ClCH2COCl/Et3N/Dioxane. Schiff base synthesis of thiazole derivatives containing Indole moiety bearing azetidine ring were synthesised by the condensation of 2-(3-(2-chloro- 3-oxo-4-phenylcyclobutyl)-1H-indol-1-yl)acetohydrazide (2) with potassium thio cyanide and substituted ketones. Then 2-(3-(2-chloro-3-oxo-4-phenylcyclobutyl)-1H-indol-1-yl)-N'-(thiazol-2-yl)acetohydrazide 4(a) was obtained. The structure of these newly synthesized compounds was characterised by 1H NMR, 13C NMR, Mass, IR, and elemental analysis. The antimicriobial activity of the novel compounds was screened by agar disc diffusion method.

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