7-Acylamino-3H-1,2-benzoxathiepine 2,2-dioxides as new isoform-selective carbonic anhydrase IX and XII inhibitors.
Antigens, Neoplasm
/ metabolism
Carbonic Anhydrase IX
/ antagonists & inhibitors
Carbonic Anhydrase Inhibitors
/ chemical synthesis
Carbonic Anhydrases
/ metabolism
Dose-Response Relationship, Drug
Humans
Isoenzymes
/ antagonists & inhibitors
Molecular Structure
Structure-Activity Relationship
Thiepins
/ chemical synthesis
Carbonic anhydrase
homosulfocoumarin
isoform-selective inhibitor
sulfocoumarin
transmembrane isoforms
Journal
Journal of enzyme inhibition and medicinal chemistry
ISSN: 1475-6374
Titre abrégé: J Enzyme Inhib Med Chem
Pays: England
ID NLM: 101150203
Informations de publication
Date de publication:
Dec 2020
Dec 2020
Historique:
entrez:
22
2
2020
pubmed:
23
2
2020
medline:
27
10
2020
Statut:
ppublish
Résumé
A series of 3H-1,2-benzoxathiepine 2,2-dioxides incorporating 7-acylamino moieties were obtained by an original procedure starting from 5-nitrosalicylaldehyde, which was treated with propenylsulfonyl chloride followed by Wittig reaction of the bis-olefin intermediate. The new derivatives, belonging to the homosulfocoumarin chemotype, were assayed as inhibitors of the zinc metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Four pharmacologically relevant human (h) isoforms were investigated, the cytosolic hCA I and II and the transmembrane, tumour-associated hCA IX and XII. No relevant inhibition of hCA I and II was observed, whereas some of the new derivatives were effective, low nanomolar hCA IX/XII inhibitors, making them of interest for investigations in situations in which the activity of these isoforms is overexpressed, such as hypoxic tumours, arthritis or cerebral ischaemia.
Identifiants
pubmed: 32079427
doi: 10.1080/14756366.2020.1722658
pmc: PMC7048192
doi:
Substances chimiques
Antigens, Neoplasm
0
Carbonic Anhydrase Inhibitors
0
Isoenzymes
0
Thiepins
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
Langues
eng
Sous-ensembles de citation
IM
Pagination
650-656Références
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