Ureidobenzenesulfonamides as Selective Carbonic Anhydrase I, IX, and XII Inhibitors-Reference-Cited by-同舟云学术

Ureidobenzenesulfonamides as Selective Carbonic Anhydrase I, IX, and XII Inhibitors

Published:2023-11-26 Issue:23 Volume:28 Page:7782
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Denner Toni C.¹^ORCID,Angeli Andrea²^ORCID,Ferraroni Marta³,Supuran Claudiu T.²^ORCID,Csuk René¹^ORCID

Affiliation:

1. Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes, Str. 2, D-06120 Halle (Saale), Germany

2. Section of Pharmaceutical Sciences, Neurofarba Department, University of Florence, Via Ugo Schiff 6, Sesto Florentino, 50019 Florence, Italy

3. Department of Chemistry “Ugo Schiff”, University of Florence, Via della Lastruccia 3-13, Sesto Fiorentino, 50019 Florence, Italy

Abstract

Sulfonamides remain an important class of drugs, especially because of their inhibitory effects on carbonic anhydrases. Herein, we have synthesized several sulfonamides and tested them for their inhibitory activity against carbonic anhydrases hCA I, hCA II, hCA IX, and hCA XII, respectively. Thereby, biphenyl- and benzylphenyl-substituted sulfonamides showed high selectivity against hCA IX and hCA XII; these enzymes are common targets in the treatment of hypoxic cancers, and noteworthy inhibitory activity was observed for several compounds toward hCA I that might be of interest for future applications to treat cerebral edema. Compound 3 (4-[3-(2-benzylphenyl)ureido]benzenesulfonamide) held an exceptionally low Ki value of 1.0 nM for hCA XII.

Funder

Elettra and BeamLine

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/23/7782/pdf

Reference34 articles.

1. Sulphamides of p-Aminobenzenesulphonic Acid;Gelmo;Vienna. J. Prakt Chem.,1908

2. The chemotherapy of bacterial infections;Mietzsch;Ber. Dtsch. Chem. Ges. A,1938

3. Chemotherapy of bacterial infections;Domagk;Dtsch. Med. Wochenschr.,1935

4. Sulfanilamide as a specific inhibitor of carbonic anhydrase;Mann;Nature,1940

5. The catalytic properties of murine carbonic anhydrase VII;Earnhardt;Biochemistry,1998