Synthesis, characterization, anticancer, antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives

Abstract

In the present study, a series of new hybrid compounds containing chalcone and methanoisoindole units 7a-n ((3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl) acryloyl) phenyl)-3a, 4,7,7a-tetrahydro-1H-4,7-methanoisoin dole-1,3(2H)-dione) were synthesized, characterized and investigated for their anticancer activity against C6 gliocarcinoma cell in rats, and antimicrobial activity against some human pathogen microorganisms. The compounds 7e, 7h, 7j, 7k, 7L and 7n showed very high anticancer activity with the inhibition range of 80.51-97.02% compared to 5-FU. Some of the compounds exhibited anti-microbial activity. Also, they evaluated for inhibition effects against human carbonic anhydrase I, and II isoenzymes (hCA I and II) with Ki values in the range of 405.26-635.68 pM for hCA I, and 245.40-489.60 pM for hCA II, respectively. These results demonstrated that 3aR, 4S, 7R, 7aS)-2-(4-((E)-3-(3-aryl) acryloyl) phenyl)-3a, 4,7,7a-tetrahy dro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives could be used in different biomedical applications. (C) 2016 Elsevier Inc. All rights reserved.