title: Synthesis and biological evaluation of new 6-s-cis locked 1,2,25-trihydroxyprevitamin D3 analogues.
abstract: An efficient synthesis of several diastereomers of 2-hydroxy substituted 1alpha,25-dihydroxyprevitamin D3 derivatives was accomplished utilizing a practical route to the A-ring synthon. The biological activity of the analogues was evaluated in vitro. All the synthesized derivatives demonstrated low affinity for the vitamin D receptor and vitamin D-binding protein compared with 1alpha,25-dihydroxyvitamin D3, the natural hormone. 1alpha,2beta,25-trihydroxy-19-nor-pre-D3 was the most potent of the analogues in inhibiting proliferation of MCF-7 cells but requires higher EC50 concentrations than 1alpha,25-dihydroxyvitamin D3.
authors.affiliation: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006 Oviedo (Asturias), Spain.
authors.forename: Laura
authors.initials: L
authors.lastname: Sánchez-Abella
authors.forename: Susana
authors.initials: S
authors.lastname: Fernández
authors.forename: Annemieke
authors.initials: A
authors.lastname: Verstuyf
authors.forename: Lieve
authors.initials: L
authors.lastname: Verlinden
authors.forename: Miguel
authors.initials: M
authors.lastname: Ferrero
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
mesh_terms: D002460:Cell Line; D049109:Cell Proliferation; D002762:Cholecalciferol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D002762:Cholecalciferol