title: Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: identification of the first inhibitor with anti-mycobacterial activity.
abstract: A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis β-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H(37)Rv strain, leading to the identification of (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(3-hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.
authors.affiliation: Cátedra de Microbiología, Virología y Parasitología, Facultad de Ciencias Médicas, Universidad Nacional de Rosario, Santa Fe 3100, 2000 Rosario, Argentina.
authors.forename: María V
authors.initials: MV
authors.lastname: Buchieri
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: Héctor R
authors.initials: HR
authors.lastname: Morbidoni
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
authors.forename: Pedro A
authors.initials: PA
authors.lastname: Colinas
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002934:Cinnamates / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: C581845:1-(2',3',4',6'-tetra-O-acetylglucopyranosyl)-4-(3-hydroxyphenyl)but-3-en-2-one; D000995:Antitubercular Agents; D002257:Carbonic Anhydrase Inhibitors; D002934:Cinnamates; D005960:Glucosides; D006027:Glycosides; C037551:cinnamoyl chloride