title: Synthesis and biological activity of 22-oxa CD-ring modified analogues of 1alpha,25-dihydroxyvitamin D3: spiro[5.5]undecane CF-ring analogues.
abstract: The synthesis and biological activity of novel CD-ring modified analogues of 22-oxa-1alpha,25-dihydroxyvitamin D(3), lacking the D-ring and featuring a connection between C-18 and C-21 (spiro[5.5]undecane CF-ring analogues), is described. The central ring system is conveniently synthesised from an achiral intermediate. The analogues have marginal binding affinity for the nVDR and possess low to moderate genomic activity.
authors.affiliation: Department of Organic Chemistry, Ghent University, Krijgslaan 281 S4, B-9000 Gent, Belgium.
authors.forename: Wim
authors.initials: W
authors.lastname: Schepens
authors.forename: Dirk Van
authors.initials: DV
authors.lastname: Van Haver
authors.forename: Maurits
authors.initials: M
authors.lastname: Vandewalle
authors.forename: Pierre J
authors.initials: PJ
authors.lastname: De Clercq
authors.forename: Roger
authors.initials: R
authors.lastname: Bouillon
authors.forename: Annemieke
authors.initials: A
authors.lastname: Verstuyf
mesh_terms: D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005786:Gene Expression Regulation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
chemical_list: D002117:Calcitriol