Design, synthesis, and biological evaluation of 3‐benzenesulfonamide‐linked 3‐hydrazinoisatin derivatives as carbonic anhydrase inhibitors

Author:

Swain Baijayantimala1,Marde Vaibhav S.1,Singh Priti1,Angeli Andrea2,Khan Abrar1,Yaddanapudi Venkata M.3,Ullah Qasim4,Supuran Claudiu T.2,Arifuddin Mohammed1ORCID

Affiliation:

1. Department of Medicinal Chemistry National Institute of Pharmaceutical Education and Research (NIPER) Hyderabad Telangana India

2. Neurofarba Department, Sezione di ScienzeFarmaceutiche e Nutraceutiche UniversitàdegliStudi di Firenze Florence Italy

3. Process Chemistry Process Technology, Department of Chemical Sciences National Institute of Pharmaceutical Education and Research (NIPER) Hyderabad Telangana India

4. Physical Sciences Section, School of Sciences Maulana Azad National Urdu University (MANUU) Hyderabad Telangana India

Abstract

AbstractA new series of isatin‐linked benzenesulfonamide derivatives (9a–w) were synthesized using the tail approach and assayed for their inhibitory potency against four different human carbonic anhydrase (hCA) isoforms, hCA I, II, IX, and XII. Most of these synthesized compounds exhibited interesting inhibition potency against isoforms hCA I, IX, and XII in the nanomolar range and by taking the standard drug acetazolamide. The most potent compounds in the case of hCA I were 9c (435.8 nM) and 9s (956.4 nM), for hCA IX, 9a (60.5 nM), 9d (95.6 nM), 9g (92.1 nM), and 9k (75.4 nM), and for hCA XII, 9p (84.5 nM). However, these compounds showed more selectivity toward hCA IX over hCA I, II, and XII. Thus, these compounds can be further developed as potential lead molecules for the development of isoform‐selective hCA IX inhibitors with further structural modifications.

Publisher

Wiley

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