Synthesis of 2α-and 2β-substituted-14-epi-previtamin D 3 and their genomic activity

Daisuke Sawada, Tomoyuki Katayama, Yuya Tsukuda, Nozomi Saito, Hiroshi Saito, Ken Ichiro Takagi, Eiji Ochiai, Seiichi Ishizuka, Kazuya Takenouchi, Atsushi Kittaka

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)


2α-and 2α-Substituted analogs of 14-epi-previtamin D3 were synthesized and isolated after thermal isomerization of 14-epi-vitamin D3 triene at 80 °C.The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were tested, and the 2a-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D 3.We found that modification at the C2 position of the seco-steroidal skeleton afforded interesting effects for biological genomic activity for the pre-vitamin D form as well as the natural vitamin D form.

Original languageEnglish
Pages (from-to)5407-5423
Number of pages17
Issue number29
Publication statusPublished - Jul 17 2010
Externally publishedYes


  • 14-epi-Previtamin D
  • Osteocalcin
  • Vitamin D
  • Vitamin Dreceptor

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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