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Bioorg Chem. 2017 Feb;70:118-125. doi: 10.1016/j.bioorg.2016.12.001. Epub 2016 Dec 23.

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.

Author information

1
Cumhuriyet University, Vocational School of Health Services, 58140 Sivas, Turkey. Electronic address: ukocyigit@cumhuriyet.edu.tr.
2
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey. Electronic address: yakup.budak@gop.edu.tr.
3
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
4
Department of Molecular Biology and Genetics, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey.
5
Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey; Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia.

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-methanoisoindole-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 405.26-635.68pM for hCA I, and 245.40-489.60pM for hCA II, respectively. These results demonstrated that 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 could be used in different biomedical applications.

KEYWORDS:

Anticancer; Antimicrobial; C6; Carbonic anhydrase; Chalcone; Isoindole

PMID:
28043719
DOI:
10.1016/j.bioorg.2016.12.001
[Indexed for MEDLINE]

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