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Convergent synthesis, chiral HPLC, and vitamin D receptor affinity of analogs of 1,25-dihydroxycholecalciferol

✍ Scribed by Małgorzata Odrzywolska; Michał Chodyński; Sebastian J. Halkes; Jan-Paul Van De Velde; Hanna Fitak; Andrzej Kutner

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
136 KB
Volume
11
Category
Article
ISSN
0899-0042

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✦ Synopsis

A series of analogs of 1,25-dihydroxycholecalciferol was obtained with an additional chiral center at the terminus of the aliphatic side chain (C-25). The analogs were obtained from (+)-(R)-and (-)-(S)-2-methylglycidols, by opening of the oxirane ring with the carbanions derived from vitamin D C 23a,24 -or C 22 -sulfones. The diastereomeric purity of the analogs was determined by high-performance liquid chromatography on a chiral stationary phase. The binding affinity of analogs for the calf thymus intracellular vitamin D receptor (VDR) was two orders of magnitude lower than that of the lead compound of this group, 24a,24b-dihomo-1,25-dihydroxycholecalciferol, and it was comparable to the affinity of analogs of 24-nor-1,25-dihydroxycholecalciferol. However, a twofold difference was observed for analogs diastereomeric at C-25 in their affinity for VDR. The diastereodifferentiation of the binding affinity was found to be specific for vitamin D vicinal 25,26-diols as it disappears for analogs where 26-hydroxyl, neighboring the C-25 chiral center, is replaced with methyl.

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