Functionalization at C-12 of 1alpha,25-dihydroxyvitamin D(3) strongly modulates the affinity for the vitamin D receptor (VDR).
The first synthesis of analogues of the natural hormone 1alpha,25-dihydroxyvitamin D(3) (1a) with substituents at C-12 is reported. The following are the relative affinities of the novel compounds for the vitamin D receptor (VDR) compared to that of 1a (100%): 1alpha,12alpha,25-(OH)(3)-D(3) (1b, 1%), 1alpha,25-(OH)(2)-12-methylene-D(3) (1c, 50%), and 1alpha,25-(OH)(2)-12beta-methyl-D(3) (1d, 440%). [structure: see text]
González-Avión
Xosé C
XC
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain.
Mouriño
Antonio
A
D000818:Animals; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D002417:Cattle; D007700:Kinetics; D011485:Protein Binding; D018167:Receptors, Calcitriol / Q000737:chemistry / Q000378:metabolism*; D013950:Thymus Gland / Q000378:metabolism
D018167:Receptors, Calcitriol; D002117:Calcitriol