Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

We synthesized and isolated 2α-substituted analogs of 14-epi-previtamin D3 after thermal isomerization at 80 °C for the first time. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were evaluated, and the 2α-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D3.

Original languageEnglish
Pages (from-to)5397-5400
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number18
DOIs
Publication statusPublished - Sep 15 2009
Externally publishedYes

Fingerprint

Osteocalcin
Isomerization
Transcriptional Activation
Hot Temperature
previtamin D(3)

Keywords

  • 14-Epi-previtamin D
  • Osteocalcin
  • Vitamin D receptor
  • Vitamin D

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry
  • Medicine(all)

Cite this

Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity. / Sawada, Daisuke; Katayama, Tomoyuki; Tsukuda, Yuya; Saito, Nozomi; Takano, Masashi; Saito, Hiroshi; Takagi, Ken ichiro; Ochiai, Eiji; Ishizuka, Seiichi; Takenouchi, Kazuya; Kittaka, Atsushi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 18, 15.09.2009, p. 5397-5400.

Research output: Contribution to journalArticle

Sawada, D, Katayama, T, Tsukuda, Y, Saito, N, Takano, M, Saito, H, Takagi, KI, Ochiai, E, Ishizuka, S, Takenouchi, K & Kittaka, A 2009, 'Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 18, pp. 5397-5400. https://doi.org/10.1016/j.bmcl.2009.07.112
Sawada, Daisuke ; Katayama, Tomoyuki ; Tsukuda, Yuya ; Saito, Nozomi ; Takano, Masashi ; Saito, Hiroshi ; Takagi, Ken ichiro ; Ochiai, Eiji ; Ishizuka, Seiichi ; Takenouchi, Kazuya ; Kittaka, Atsushi. / Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 18. pp. 5397-5400.
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