Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)

Susumi Hatakeyama, Toshio Okano, Junji Maeyama, Tomoyuki Esumi, Hiroko Hiyamizu, Yoshiharu Iwabuchi, Kimie Nakagawa, Keiichi Ozono, Akira Kawase, Noboru Kubodera

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).

Original languageEnglish
Pages (from-to)403-415
Number of pages13
JournalBioorganic and Medicinal Chemistry
Volume9
Issue number2
DOIs
Publication statusPublished - 2001 Apr 10
Externally publishedYes

ASJC Scopus subject areas

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

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