Concise synthesis and biological activities of 2α-alkyl- and 2α-(ω-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D 3

Shinobu Honzawa, Yoshitomo Suhara, Ken Ichi Nihei, Nozomi Saito, Seishi Kishimoto, Toshie Fujishima, Masaaki Kurihara, Takayuki Sugiura, Keizo Waku, Hiroaki Takayama, Atsushi Kittaka

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

We found a concise route to the Trost A-ring precursor enyne for synthesizing 2α-alkylated 1α,25-dihydroxyvitamin D3 (1) from D-glucose. The enynes were coupled with the 20-epi-CD ring part to study the effect of the double modification of 2α-substitution and 20-epimerization upon biological activities of 1. The novel three analogues of 2α-alkyl- and four analogues of 2α-(ω -hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D3 (5b-d and 6a-d) showed higher binding affinity for vitamin D receptor (VDR) and more potent activity in induction of HL-60 cell differentiation than those of the natural hormone 1.

Original languageEnglish
Pages (from-to)3503-3506
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number20
DOIs
Publication statusPublished - 2003 Oct 20

ASJC Scopus subject areas

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

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    Honzawa, S., Suhara, Y., Nihei, K. I., Saito, N., Kishimoto, S., Fujishima, T., Kurihara, M., Sugiura, T., Waku, K., Takayama, H., & Kittaka, A. (2003). Concise synthesis and biological activities of 2α-alkyl- and 2α-(ω-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D 3. Bioorganic and Medicinal Chemistry Letters, 13(20), 3503-3506. https://doi.org/10.1016/S0960-894X(03)00739-X