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

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)267-276
Number of pages10
JournalSteroids
Volume66
Issue number3-5
DOIs
Publication statusPublished - 2001 May 1
Externally publishedYes

Keywords

  • 1α,25-Dihydroxy-2β-(3-hydroxypropoxy)vitamin D
  • 1α,25-Dihydroxyvitamin D
  • 24-Hydroxylated ED-71
  • ED-71
  • Sterol

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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