Benzimidazole derivatives as potent and isoform selective tumor-associated carbonic anhydrase IX/XII inhibitors.
Benzimidazole
Carbonic anhydrase
Carboxylic acid
Hydroxamic acid
Sulfonamide
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
01 2020
01 2020
Historique:
received:
08
10
2019
revised:
06
12
2019
accepted:
21
12
2019
pubmed:
10
1
2020
medline:
9
3
2021
entrez:
10
1
2020
Statut:
ppublish
Résumé
We describe the synthesis of a series of 2-arylbenzimidazole derivatives bearing sulfonamide functionality (4a-d, 7a-c and 10) as well as hydroxamic acid (15a-b), carboxylic acid (16a-b), carboxamide (17a-b) and boronic acid (22a-b and 26) functionalities, which act as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. The newly synthesized benzimidazole derivatives were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IX, and XII), and especially the sulfonamide-containing benzimidazoles demonstrated intriguing inhibitory activity against tumor associated CA IX and XII with K
Identifiants
pubmed: 31915112
pii: S0045-2068(19)31655-4
doi: 10.1016/j.bioorg.2019.103544
pii:
doi:
Substances chimiques
Antigens, Neoplasm
0
Antineoplastic Agents
0
Benzimidazoles
0
Carbonic Anhydrase Inhibitors
0
CA9 protein, human
EC 4.2.1.1
Carbonic Anhydrase IX
EC 4.2.1.1
Carbonic Anhydrases
EC 4.2.1.1
carbonic anhydrase XII
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
103544Informations de copyright
Copyright © 2019 Elsevier Inc. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.