title: Synthesis and evaluation of α-, β-glucosidase inhibition of 1-N-carboxamide-1-azafagomines and 5-epi-1-azafagomines.
abstract: 1-N-Carboxamide 1-azafagomines and 5-epi-1-azafagomines were obtained from 1-azafagomine and 5-epi-1-azafagomine. The hydroxyl groups and the N-2 pyridazine position were protected prior to reaction with different isocyanates to form ureas. Protective groups were removed leading to the target compounds in 18-23% global yields. Final compounds were tested towards α- and β-glucosidases.
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
authors.forename: Raquel
authors.initials: R
authors.lastname: Mendes
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
authors.forename: Vera C M
authors.initials: VC
authors.lastname: Duarte
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
authors.forename: António
authors.initials: A
authors.lastname: Gil Fortes
authors.affiliation: Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. Electronic address: mja@quimica.uminho.pt.
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Alves
mesh_terms: D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry; D012441:Saccharomyces cerevisiae / Q000737:chemistry / Q000201:enzymology; D029701:Saccharomyces cerevisiae Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry; D000520:alpha-Glucosidases / Q000737:chemistry* / Q000302:isolation & purification; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: C414749:1-azafagomine; D065089:Glycoside Hydrolase Inhibitors; D007212:Indolizines; D017953:Isocyanates; D029701:Saccharomyces cerevisiae Proteins; D014508:Urea; D000520:alpha-Glucosidases; D001617:beta-Glucosidase
keywords: 1-Azafagomines; Aza-Diels–Alder; Glucosidases inhibition