Synthesis and Anticancer Activity of Novel Amide Tagged Trifluoromethyl Indole and Pyrimido Indole Derivatives

Manoj Kumar Mandadi, Ramana Reddy Bobbala, Balakrishna Kolli*, and Rambabu Gundla*,

Department of Chemistry, GITAM University, Rudraram, Hyderabad-502329, India

*Corresponding authors: E-mail: rgundla@gitam.edu

Abstract

A series of novel amide tagged trifluoromethyl indole and pyrimido indole derivatives 4a-e & 5a-e and 6a-d & 7a-d were synthesized from 4-methyl-2-(methylamino)-6-(trifluoromethyl)isophthalonitrile (1) on reaction with bromoethyl acetate to obtain 2a and 2b isomers. Compound 2a treated with hydrazine hydrate followed by Schiff base reaction to get compounds 4a-e. In another way, compound 2a on reaction with aliphatic primary amine to get compounds 6a-d. For cyclization, compounds 4a-e & 6a-d treated with trifluoroacetic acid to obtain compounds 5a-e and 7a-d, respectively. All the synthesized compounds 4a-e & 5a-e and 6a-d & 7a-d were tested for anticancer activity against four human cancer cell lines such as A549-lung cancer (CCL-185), MCF7-breast cancer (HTB-22), DU145-prostate cancer (HTB-81) and HeLa-cervical cancer (CCL-2). Compounds 9e and 9f were found to have promising anticancer activity at micromolar concentration.

Keywords

Trifluoromethyl indole, Pyrimido indole, Cyclization, Schiff base, Anticancer activity.

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