期刊
JOURNAL OF MEDICINAL CHEMISTRY
卷 59, 期 2, 页码 721-732出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jmedchem.5b01771
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资金
- Italian Ministry of Education, University and Research (MIUR, PRIN) [2010N3T9M4]
- Italian-French University (Vinci)
- University of Chieti-Pescara
- Centre National de la Recherche Scientifique (CNRS)
- University of Reims
- European Research Council (ERC)
Benzenesulfonamides bearing various substituted (hetero)aryl rings in the para-position were prepared by palladium nanoparticle-catalyzed Suzuki-Miyaura cross-coupling reactions and evaluated as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors against isoforms hCA I, II, IX, and XII. Most of the prepared sulfonamides showed low inhibition against hCA I isoform, whereas the other cytosolic isoenzyme, hCA II, was strongly affected. The major part of these new derivatives acted as potent inhibitors of the tumor-associated isoform hCA XII. An opposite trend was observed for phenyl, naphthyl, and various heteroaryl substituted benzenesulfonamides which displayed subnanomolar hCA IX inhibition while poorly inhibiting the other tumor-associated isoform hCA XII. The inhibition potency and influence of the partially restricted arylaryl bond rotation on the activity/selectivity were rationalized by means of X-ray crystallography of the adducts of hCA II with several 4-arylbenzenesulfonamides.
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