Synthesis and Biological Evaluation of 4-Substituted Vitamin D and 14-Epi-Previtamin D Analogs

Synthesis and Biological Evaluation of 4-Substituted Vitamin D and 14-Epi-Previtamin D Analogs

We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D3 (1α,25(OH)2D3, 1) and its C14-epimer with the previtamin D3 form of 14-epi-1α,25(OH)2preD3 (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evalua...

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Veröffentlicht in:Chemical & Pharmaceutical Bulletin 2009/12/01, Vol.57(12), pp.1431-1433
Hauptverfasser: Sawada, Daisuke, Tsukuda, Yuya, Saito, Hiroshi, Takagi, Ken-ichiro, Horie, Kyouhei, Ochiai, Eiji, Takenouchi, Kazuya, Kittaka, Atsushi
Format: Artikel
Sprache:eng
Schlagworte:
Binding Sites
C4-modified seco-steroid
Cholecalciferol - chemical synthesis
Cholecalciferol - genetics
Cholecalciferol - metabolism
Humans
Molecular Structure
Osteoblasts - metabolism
osteocalcin
previtamin D3
Receptors, Calcitriol - chemistry
Receptors, Calcitriol - metabolism
Vitamin D - analogs & derivatives
Vitamin D - chemistry
vitamin D receptor
vitamin D3
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Zusammenfassung:We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D3 (1α,25(OH)2D3, 1) and its C14-epimer with the previtamin D3 form of 14-epi-1α,25(OH)2preD3 (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evaluated, and had lower activity than the natural hormone (1) and 14-epi-pre1, respectively.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.57.1431