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 journalArticle

13 Citations (Scopus)

Abstract

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
JournalTetrahedron
Volume66
Issue number29
DOIs
Publication statusPublished - Jul 17 2010
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of 2α-and 2β-substituted-14-epi-previtamin D <sub>3</sub> and their genomic activity'. Together they form a unique fingerprint.

  • Cite this

    Sawada, D., Katayama, T., Tsukuda, Y., Saito, N., Saito, H., Takagi, K. I., Ochiai, E., Ishizuka, S., Takenouchi, K., & Kittaka, A. (2010). Synthesis of 2α-and 2β-substituted-14-epi-previtamin D 3 and their genomic activity. Tetrahedron, 66(29), 5407-5423. https://doi.org/10.1016/j.tet.2010.05.028