title: Reversal of diastereoselectivity in the synthesis of peptidomimetic 3-carboxamide-1,4-benzodiazepin-5-ones.
abstract: Enantiopure 3-carboxamide-1,4-benzodiazepin-5-ones were synthesized via the Ugi reaction followed by the Staudinger/aza-Wittig or reduction reactions in only two steps. A complete reversal of diastereoselectivity was achieved depending on the cyclization methodology employed. The different orientation of the C3 substituent in our 3-substituted 1,4-benzodiazepin-5-ones with respect to the most studied 1,4-benzodiazepin-2-ones makes them complementary in the development of new drugs because the primary source of binding selectivity of 1,4-benzodiazepines is the selective recognition of ligand conformations by the receptor.
authors.affiliation: Chemistry Department, Faculty of Science, University of Burgos , 09001 Burgos, Spain.
authors.forename: Pablo
authors.initials: P
authors.lastname: Pertejo
authors.forename: Nazaret
authors.initials: N
authors.lastname: Corres
authors.forename: Tomás
authors.initials: T
authors.lastname: Torroba
authors.forename: María
authors.initials: M
authors.lastname: García-Valverde
mesh_terms: D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D057786:Peptidomimetics; D013237:Stereoisomerism
chemical_list: D001570:Benzodiazepinones; D006576:Heterocyclic Compounds, 4 or More Rings; D057786:Peptidomimetics