Synthesis, biological evaluation, and docking studies of novel thiourea derivatives of bisindolylmethane as carbonic anhydrase II inhibitor

• Published in: Bioorganic Chemistry
• Main Author: Imran S.; Taha M.; Ismail N.H.; Fayyaz S.; Khan K.M.; Choudhary M.I.
• Format: Article
• Language: English
• Published: Academic Press Inc. 2015
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84939209512&doi=10.1016%2fj.bioorg.2015.08.001&partnerID=40&md5=0dc9b1616d3254a95a28d2afe565dbe4
• ISSN: 452068
• DOI: 10.1016/j.bioorg.2015.08.001

Abstract This article describes discovery of 29 novel bisindolylmethanes consisting of thiourea moiety, which had been synthesized through three steps. These novel bisindolylmethane derivatives evaluated for their potential inhibitory activity against carbonic anhydrase (CA) II. The results for in vitro assay of carbonic anhydrase II inhibition activity showed that some of the compounds are capable of suppressing the activity of carbonic anhydrase II. Bisindoles having halogen at fifth position showed better inhibitory activity as compared to unsubstituted bisindoles. Derivatives showing inhibition activity docked to further, understand the binding behavior of these compounds with carbonic anhydrase II. Docking studies for the active compound 3j showed that nitro substituent at para position fits into the core of the active site. The nitro substituent of compound 3j is capable of interacting with Zn ion. This interaction believed to be the main factor causing inhibition activity to take place. © 2015 Elsevier Inc.