A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3: Remarkably high affinity to vitamin D receptor

Atsushi Kittaka, Yoshitomo Suhara, Hitoshi Takayanagi, Toshie Fujishima, Masaaki Kurihara, Hiroaki Takayama

研究成果: Article査読

81 被引用数 (Scopus)

抄録

(equation presented) A convenient and potentially valuable synthetic approach to the novel 2α-functionalized 1α,25-dihydroxyvitamin D3 [1α,25(OH)2D3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2α-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2α-(ω-hydroxyalkoxy)-1α,25(OH)2D3 derivatives, 1a and 1b showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

本文言語English
ページ(範囲)2619-2622
ページ数4
ジャーナルOrganic Letters
2
17
DOI
出版ステータスPublished - 2000 8 24
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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