title: C-glycosides incorporating the 6-methoxy-2-naphthyl moiety are selective inhibitors of fungal and bacterial carbonic anhydrases.
abstract: A small series of C-glycosides containing the methoxyaryl moieties was tested for the inhibition of the β-class carbonic anhydrases (CAs, EC 4.2.1.1) from Cryptococcus neoformans and Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. The deprotected glycosides incorporating the 6-methoxy-2-naphthyl moiety showed the best inhibition profile and therefore represent leads for the development of novel anti-infectives with a new mechanism of action.
authors.affiliation: a LADECOR, Departamento de Química , Facultad de Ciencias Exactas, Universidad Nacional de La Plata , La Plata , Argentina .
authors.forename: Leonardo E
authors.initials: LE
authors.lastname: Riafrecha
authors.forename: Daniela
authors.initials: D
authors.lastname: Vullo
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
authors.forename: Pedro A
authors.initials: PA
authors.lastname: Colinas
mesh_terms: D041021:Brucella suis / Q000201:enzymology*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000378:metabolism*; D003455:Cryptococcus neoformans / Q000201:enzymology*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D009281:Naphthalenes / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D006027:Glycosides; D007527:Isoenzymes; D009281:Naphthalenes; D002256:Carbonic Anhydrases
keywords: Carbohydrate; carbonic anhydrase; pathogen