Synthesis of 24,24-difluoro-1,3-cis-25-dihydroxy-19-norvitamin D3 derivatives and evaluation of their vitamin D receptor-binding affinity

Tanima Biswas, Yusuke Akagi, Kosuke Usuda, Koji Yasui, Isao Shimizu, Mayumi Okamoto, Motonari Uesugi, Seijiro Hosokawa*, Kazuo Nagasawa

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Two vitamin D3 derivatives, namely 24,24-difluoro-1β,3β,25-dihydroxy-19-norvitamin D3 (6a) and 24,24-difluoro-1α,3α,25-dihydroxy-19-norvitamin D3 (6b), were synthesized via a convergent route employing Julia-Kocienski olefination as a key step. Compounds 6a and b bound to vitamin D receptor (VDR) with IC50 values of 64.8 and 57.6 nM, respectively, exhibiting about 400- and 30-fold greater binding affinity than the corresponding non-fluorinated derivatives 5a and b.

Original languageEnglish
Pages (from-to)1387-1391
Number of pages5
JournalBiological and Pharmaceutical Bulletin
Issue number8
Publication statusPublished - 2016


  • 24,24-difluoro-19-norvitamin D
  • Julia-Kocienski coupling
  • Vitamin D
  • Vitamin D receptor binding
  • cis-A ring synthon

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science


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