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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.JE

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.

Authors+Show Affiliations

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

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28753093

Citation

Abdoli, Morteza, et al. "Synthesis and Carbonic Anhydrase I, II, VII, and IX Inhibition Studies With a Series of Benzo[d]thiazole-5- and 6-sulfonamides." Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 32, no. 1, 2017, pp. 1071-1078.
Abdoli M, Angeli A, Bozdag M, et al. 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;32(1):1071-1078.
Abdoli, M., Angeli, A., Bozdag, M., Carta, F., Kakanejadifard, A., Saeidian, H., & Supuran, C. T. (2017). Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 1071-1078. https://doi.org/10.1080/14756366.2017.1356295
Abdoli M, et al. 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;32(1):1071-1078. PubMed PMID: 28753093.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides. AU - Abdoli,Morteza, AU - Angeli,Andrea, AU - Bozdag,Murat, AU - Carta,Fabrizio, AU - Kakanejadifard,Ali, AU - Saeidian,Hamid, AU - Supuran,Claudiu T, PY - 2017/7/29/entrez PY - 2017/7/29/pubmed PY - 2017/10/11/medline KW - Carbonic anhydrase KW - benzo[d]thiazole KW - inhibitor KW - scaffold KW - sulfonamide SP - 1071 EP - 1078 JF - Journal of enzyme inhibition and medicinal chemistry JO - J Enzyme Inhib Med Chem VL - 32 IS - 1 N2 - 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. SN - 1475-6374 UR - https://www.unboundmedicine.com/medline/citation/28753093/Synthesis_and_carbonic_anhydrase_I_II_VII_and_IX_inhibition_studies_with_a_series_of_benzo[d]thiazole_5__and_6_sulfonamides_ L2 - http://www.tandfonline.com/doi/full/10.1080/14756366.2017.1356295 DB - PRIME DP - Unbound Medicine ER -