Synthesis and biological characterization of 1α,24,25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (24-hydroxylated ED-71)

Susumi Hatakeyama, Akira Kawase, Yasushi Uchiyama, Junji Maeyama, Yoshiharu Iwabuchi, Noboru Kubodera

研究成果: Article査読

28 被引用数 (Scopus)

抄録

24-Hydroxylated derivatives were synthesized in 24(R) and 24(S) forms by the convergent method as analogs related to 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3. In the convergent synthesis, the A-ring fragment, synthesized from diethyl D-tartarate, and the C/D-ring fragments in 24(R) and 24(S) forms (vitamin D numbering), obtained from vitamin D2 via the Inhoffen-Lythgoe diol, were coupled in moderate yields to give 1α,24(R),25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3 and 1α,24(S),25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3. In preliminary biological evaluations, 24-hydroxylation of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 caused weakened affinity to vitamin D binding protein in vitro and less calcemic activity in vivo compared to the parent compound. While the affinity to vitamin D receptor in 24(R) epimer was sustained, the affinity in 24(S) epimer was less than that of the parent compound.

本文言語English
ページ(範囲)267-276
ページ数10
ジャーナルSteroids
66
3-5
DOI
出版ステータスPublished - 2001 5 1
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 分子生物学
  • 内分泌学
  • 薬理学
  • 臨床生化学
  • 有機化学

フィンガープリント

「Synthesis and biological characterization of 1α,24,25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D<sub>3</sub> (24-hydroxylated ED-71)」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル