title: Design and efficient synthesis of new stable 1alpha,25-dihydroxy-19-norvitamin D3 analogues containing amide bond.
abstract: The design and synthesis of new 1alpha,25-dihydroxy-19-norvitamin D(3) analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16 was synthesized from Grundmann's ketone. Coupling those parts gave desired 3a-c in good yield. This strategy can be applied in combinatorial chemistry; therefore, those compounds would be applicable as useful tools in the development of new drugs.
authors.affiliation: Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan.
authors.forename: Yoshitomo
authors.initials: Y
authors.lastname: Suhara
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kittaka
authors.forename: Keiichiro
authors.initials: K
authors.lastname: Ono
authors.forename: Masaaki
authors.initials: M
authors.lastname: Kurihara
authors.forename: Toshie
authors.initials: T
authors.lastname: Fujishima
authors.forename: Akihiro
authors.initials: A
authors.lastname: Yoshida
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Takayama
mesh_terms: D000577:Amides / Q000138:chemical synthesis; D001665:Binding Sites; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D008958:Models, Molecular; D018167:Receptors, Calcitriol / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D018167:Receptors, Calcitriol; C083610:1,25-dihydroxy-19-norvitamin D3; D002117:Calcitriol