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

11 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

Fingerprint

Vitamin D
Cholecalciferol
Osteocalcin
Isomerization
Skeleton
Transcriptional Activation
Hot Temperature
previtamin D(3)

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Sawada, D., Katayama, T., Tsukuda, Y., Saito, N., Saito, H., Takagi, K. I., ... 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

Synthesis of 2α-and 2β-substituted-14-epi-previtamin D 3 and their genomic activity. / Sawada, Daisuke; Katayama, Tomoyuki; Tsukuda, Yuya; Saito, Nozomi; Saito, Hiroshi; Takagi, Ken Ichiro; Ochiai, Eiji; Ishizuka, Seiichi; Takenouchi, Kazuya; Kittaka, Atsushi.

In: Tetrahedron, Vol. 66, No. 29, 17.07.2010, p. 5407-5423.

Research output: Contribution to journalArticle

Sawada, D, Katayama, T, Tsukuda, Y, Saito, N, Saito, H, Takagi, KI, 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, vol. 66, no. 29, pp. 5407-5423. https://doi.org/10.1016/j.tet.2010.05.028
Sawada, Daisuke ; Katayama, Tomoyuki ; Tsukuda, Yuya ; Saito, Nozomi ; Saito, Hiroshi ; Takagi, Ken Ichiro ; Ochiai, Eiji ; Ishizuka, Seiichi ; Takenouchi, Kazuya ; Kittaka, Atsushi. / Synthesis of 2α-and 2β-substituted-14-epi-previtamin D 3 and their genomic activity. In: Tetrahedron. 2010 ; Vol. 66, No. 29. pp. 5407-5423.
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