title: Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases.
abstract: A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.
authors.affiliation: LADECOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 y 115, 1900 La Plata, Argentina.
authors.forename: Leonardo E
authors.initials: LE
authors.lastname: Riafrecha
authors.forename: Oscar M
authors.initials: OM
authors.lastname: Rodríguez
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: D000818:Animals; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002256:Carbonic Anhydrases / Q000737:chemistry* / Q000378:metabolism; D002935:Cinnamomum zeylanicum / Q000737:chemistry*; D006027:Glycosides; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D007700:Kinetics; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D011485:Protein Binding
chemical_list: C438934:C-glycoside; D002257:Carbonic Anhydrase Inhibitors; D006027:Glycosides; D007527:Isoenzymes; D009005:Monosaccharides; D002256:Carbonic Anhydrases