Two series of novel bis(indole) analogues viz., N′-((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a–f) and N′-((5-substituted-1-(3-methylbut-2-enyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a–f) were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial, anticancer activities and structure and activity relationship (SAR) was investigated. Compounds 7a, 7c and 8a were found to be active in antimicrobial screening. Anticancer screening reveals that Compound 7c was active against HeLa cell line with an IC50 of 43.1 μM and compound 7d was found to be interesting candidate with an IC50 of 26.0 and 30.2 μM against Colo-205 and Hep G2 cell lines respectively. Keywords: Indole-3-acylhydrazides, Indole-3-carboxaldehyde, N-prenylated indole-3-carboxaldehyde, Bis(indole) analogues, Antimicrobial activity, Anticancer activity
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