1. Academic Validation
  2. Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides

Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides

  • J Enzyme Inhib Med Chem. 2017 Dec;32(1):1071-1078. doi: 10.1080/14756366.2017.1356295.
Morteza Abdoli 1 2 3 Andrea Angeli 3 Murat Bozdag 2 Fabrizio Carta 2 3 Ali Kakanejadifard 1 Hamid Saeidian 4 Claudiu T Supuran 3
Affiliations

Affiliations

  • 1 a Department of Chemistry, Faculty of Science , Lorestan University , Khorramabad , Iran.
  • 2 b Dipartimento di Chimica, Laboratorio di Chimica Bioinorganica , Università degli Studi di Firenze , Sesto Fiorentino, Florence , Italy.
  • 3 c Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche, Polo Scientifico , Università degli Studi di Firenze , Sesto Fiorentino, Florence , Italy.
  • 4 d Department of Science , Payame Noor University (PNU) , Tehran , Iran.
Abstract

A series of benzo[d]thiazole-5- and 6-sulfonamides has been synthesized and investigated for the inhibition of several human (h) Carbonic Anhydrase (CA, EC 4.2.1.1) isoforms, using ethoxzolamide (EZA) as lead molecule. 2-Amino-substituted, 2-acylamino- and halogenated (bromo-and iodo-derivatives at the heterocyclic ring) compounds led to several interesting inhibitors against the cytosolic hCA I, II and VII, as well as the transmembrane, tumor-associated hCA IX isoforms. Several subnanomolar/low nanomolar, isoform-selective sulfonamide inhibitors targeting hCA II, VII and IX were detected. The sharp structure-activity relationship for CA inhibition with this small series of derivatives, with important changes of activity observed even after minor changes in the scaffold or at the 2-amino moiety, make this class of scarcely investigated sulfonamides of particular interest for further investigations.

Keywords

Carbonic anhydrase; benzo[d]thiazole; inhibitor; scaffold; sulfonamide.

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