title: Search for alpha-glucosidase inhibitors: new N-substituted valienamine and conduramine F-1 derivatives.
abstract: A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (+/-)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward alpha-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.
authors.affiliation: Laboratoire de glycochimie et de synthèse asymétrique, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC, BCH, CH-1015 Lausanne-Dorigny, Switzerland.
authors.forename: Robert
authors.initials: R
authors.lastname: Łysek
authors.forename: Catherine
authors.initials: C
authors.lastname: Schütz
authors.forename: Sylvain
authors.initials: S
authors.lastname: Favre
authors.forename: Anthony C
authors.initials: AC
authors.lastname: O'Sullivan
authors.forename: Christian
authors.initials: C
authors.lastname: Pillonel
authors.forename: Thomas
authors.initials: T
authors.lastname: Krülle
authors.forename: Pierre M J
authors.initials: PM
authors.lastname: Jung
authors.forename: Imma
authors.initials: I
authors.lastname: Clotet-Codina
authors.forename: José A
authors.initials: JA
authors.lastname: Esté
authors.forename: Pierre
authors.initials: P
authors.lastname: Vogel
mesh_terms: D003511:Cyclohexanols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D053138:Cyclohexenes; D003514:Cyclohexylamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D006595:Hexosamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C514594:6-aminocyclohex-4-ene-1,2,3-triol; D003511:Cyclohexanols; D053138:Cyclohexenes; D003514:Cyclohexylamines; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D006595:Hexosamines; C030791:valienamine