Ureidosulfocoumarin Derivatives As Selective and Potent Carbonic Anhydrase IX and XII Inhibitors.
Carbonic anhydrases
Non-classical inhibition
Sulfocoumarins
hCA IX
hCA XII
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
04 03 2022
04 03 2022
Historique:
revised:
10
12
2021
received:
19
11
2021
pubmed:
14
12
2021
medline:
3
5
2022
entrez:
13
12
2021
Statut:
ppublish
Résumé
Owing to severe allergic reactions (anaphylaxis) and resistance exhibited by sulfonamide-based carbonic anhydrase (CA) inhibitors, non-classical or non-sulfonamide CA inhibitors are gaining increased attention by medicinal chemists. In this context, we report the design and synthesis of 30 new non-sulfonamide sulfocoumarin derivatives as CA inhibitors. They were investigated against hCA I and II (cytosolic isozymes) as well as hCA IX and XII (transmembrane, tumor-associated enzymes). All compounds showed prominent selectivity for the tumor-associated isoenzymes hCA IX and XII over the cytosolic isoenzymes hCA I and II. Among all synthesized compounds, 1-(2,2-dioxidobenzo[e][1,2]oxathiin-6-yl)-3-(o-tolyl)urea(5 j)and1-(3-fluorophenyl)-3-(8-methoxy-2,2-dioxidobenzo[e][1,2]oxathiin-6-yl)urea(5 q)were found to be more potent and to have better inhibition constant values against hCA IX than the standard acetazolamide (AAZ), with K
Identifiants
pubmed: 34898017
doi: 10.1002/cmdc.202100725
doi:
Substances chimiques
Antigens, Neoplasm
0
Carbonic Anhydrase Inhibitors
0
Isoenzymes
0
Oxathiins
0
Urea
8W8T17847W
Carbonic Anhydrase IX
EC 4.2.1.1
Carbonic Anhydrases
EC 4.2.1.1
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202100725Informations de copyright
© 2021 Wiley-VCH GmbH.
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