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

研究成果: Article査読

26 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3503-3506
ページ数4
ジャーナルBioorganic and Medicinal Chemistry Letters
13
20
DOI
出版ステータスPublished - 2003 10月 20
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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