Synthesis of 25-hydroxy-19-norvitamin D3 analogs and their antiproliferative activities on prostate cells

Midori A. Arai, Ryuji Tsutsumi, Hideki Hara, Tai C. Chen, Toshiyuki Sakaki, Naoko Urushino, Kuniyo Inouye, Atsushi Kittaka

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15 Citations (Scopus)

Abstract

Synthesis of 25-hydroxy-19-norvitamin D3 derivatives as prohormone type agents for anti-prostate diseases was accomplished utilizing Julia-type olefination. Synthesized compounds showed potent antiproliferative activity on an immortalized normal prostate cell line, PZ-HPV-7, which has high 1α-hydroxylase activity. Furthermore, we demonstrated that 25-hydroxy-19-norvitamin D3 was hydroxylated at the 1α position to form 1α,25-dihydroxy-19-norvitamin D3 by a recombinant human 1α-hydroxylase (CYP27B1) in a cell-free system.

Original languageEnglish
Pages (from-to)469-479
Number of pages11
JournalHeterocycles
Volume66
Issue number1
DOIs
Publication statusPublished - 2005 Dec 31

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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    Arai, M. A., Tsutsumi, R., Hara, H., Chen, T. C., Sakaki, T., Urushino, N., Inouye, K., & Kittaka, A. (2005). Synthesis of 25-hydroxy-19-norvitamin D3 analogs and their antiproliferative activities on prostate cells. Heterocycles, 66(1), 469-479. https://doi.org/10.3987/com-05-s(k)56