title: Synthesis and evaluation of a 3-position diastereomer of 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 (ED-71).
abstract: A 3-position diastereomer of 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 (ED-71, 2), 3-epi-ED-71 (4), was synthesized by the convergent method coupling the A-ring fragment (5) with the C/D-ring fragment (6). As the results of preliminary in vitro biological evaluation of 3-epi-ED-71 (4), the inhibition of parathyroid hormone secretion in bovine parathyroid cells and binding affinity to human recombinant vitamin D receptor and to human vitamin D binding protein in comparison with ED-71 (2), 1alpha,25-dihydroxyvitamin D3 (1,25(OH)2D3, 1), and 3-epi-1,25(OH)2D3 (3) are described.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama
authors.forename: Satoshi
authors.initials: S
authors.lastname: Nagashima
authors.forename: Naoko
authors.initials: N
authors.lastname: Imai
authors.forename: Keisuke
authors.initials: K
authors.lastname: Takahashi
authors.forename: Jun
authors.initials: J
authors.lastname: Ishihara
authors.forename: Atsuko
authors.initials: A
authors.lastname: Sugita
authors.forename: Takeshi
authors.initials: T
authors.lastname: Nihei
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Saito
authors.forename: Fumiaki
authors.initials: F
authors.lastname: Takahashi
authors.forename: Noboru
authors.initials: N
authors.lastname: Kubodera
mesh_terms: D000818:Animals; D002417:Cattle; D002762:Cholecalciferol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010280:Parathyroid Glands / Q000166:cytology; D010281:Parathyroid Hormone / Q000037:antagonists & inhibitors / Q000378:metabolism; D011485:Protein Binding; D018167:Receptors, Calcitriol / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D010281:Parathyroid Hormone; D018167:Receptors, Calcitriol; D002762:Cholecalciferol