Versatile Diazomethane Sulfonamide for Expedited Exploration of Azole-Based Carbonic Anhydrase Inhibitors via [3+2] Cycloaddition.
Carbonic Anhydrase Inhibitors
/ pharmacology
Molecular Structure
Structure-Activity Relationship
Diazomethane
Carbonic Anhydrase IX
/ metabolism
Azoles
/ pharmacology
Carbonic Anhydrase I
/ metabolism
Carbonic Anhydrase II
Cycloaddition Reaction
Carbonic Anhydrases
/ metabolism
Sulfonamides
/ pharmacology
Protein Isoforms
C−H diazomethane sulfonamide
[3+2] dipolar cycloaddition
carbonic anhydrase
isoform selectivity
p-methoxybenzyl protecting group
primary sulfonamide
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
16 05 2023
16 05 2023
Historique:
revised:
28
02
2023
received:
10
11
2022
medline:
17
5
2023
pubmed:
13
4
2023
entrez:
12
4
2023
Statut:
ppublish
Résumé
A newly introduced diazo reagent, 1-diazo-N,N-bis(4-methoxybenzyl)methanesulfonamide, enables access to a range of azole-based primary sulfonamides via [3+2] cycloaddition followed by protecting group removal. Such compounds are representative of the sulfonamide chemical space highly relevant but hitherto not investigated in the context of inhibition of therapeutically relevant isoforms of carbonic anhydrase enzyme. Using this reagent, three sets of primary sulfonamides based on pyrazole, 1,2,3-triazole and tetrazole cores were synthesized and profiled for inhibition of tumor-associated hCA IX and XII isoforms as well as abundant cytosolic hCA I and II isoforms. Using virtual library design and docking prioritization tool of the Schrödinger suite, one of the promising leads was evolved into a dual hCA IX/XII inhibitor with excellent selectivity over off-target hCA I and II. The new synthetic strategy to access azole-based primary sulfonamides will support the discovery of novel, isoform-selective inhibitors of carbonic anhydrase within the poorly explored azole chemical space.
Identifiants
pubmed: 37042451
doi: 10.1002/cmdc.202200607
doi:
Substances chimiques
Carbonic Anhydrase Inhibitors
0
Diazomethane
60A625P70P
Carbonic Anhydrase IX
EC 4.2.1.1
Azoles
0
Carbonic Anhydrase I
EC 4.2.1.-
Carbonic Anhydrase II
EC 4.2.1.-
Carbonic Anhydrases
EC 4.2.1.1
Sulfonamides
0
Protein Isoforms
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200607Informations de copyright
© 2023 Wiley-VCH GmbH.
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