Total synthesis of 25-hydroxy-16,23E-diene vitamin D3 and 1α,25-dihydroxy-16,23E-diene vitamin D3: Separation of genomic and nongenomic vitamin D activities

Marek M. Kabat, Walter Burger, Sandra Guggino, Bernard Hennessy, Jerome A. Iacobelli, Kazuhiro Takeuchi, Milan R. Uskokovic

Research output: Contribution to journalArticle

Abstract

Separation of genomic and nongenomic vitamin D activities was achieved by structural modification of 1,25-dihydroxy vitamin D3 by introduction of 16 and 23E double bonds. The modified compound 3, lacking a 1α-hydroxy group, exhibits only nongenomic activity. Its 1α-hydroxy relative 4 expresses fully both genomic and nongenomic activities. A total synthesis of analogues 3 and 4 is described. Copyright (C) 1997 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)2051-2059
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume6
Issue number11
DOIs
StatePublished - Nov 1998

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Cholecalciferol
Vitamin D
dihydroxy-vitamin D3
25-hydroxy-16,23-diene vitamin D3

Keywords

  • Calcium channel
  • Genomic effect
  • Nongenomic effect
  • Transcriptional effect
  • Vitamin D analogues

ASJC Scopus subject areas

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

Cite this

Total synthesis of 25-hydroxy-16,23E-diene vitamin D3 and 1α,25-dihydroxy-16,23E-diene vitamin D3 : Separation of genomic and nongenomic vitamin D activities. / Kabat, Marek M.; Burger, Walter; Guggino, Sandra; Hennessy, Bernard; Iacobelli, Jerome A.; Takeuchi, Kazuhiro; Uskokovic, Milan R.

In: Bioorganic and Medicinal Chemistry, Vol. 6, No. 11, 11.1998, p. 2051-2059.

Research output: Contribution to journalArticle

Kabat, Marek M. ; Burger, Walter ; Guggino, Sandra ; Hennessy, Bernard ; Iacobelli, Jerome A. ; Takeuchi, Kazuhiro ; Uskokovic, Milan R. / Total synthesis of 25-hydroxy-16,23E-diene vitamin D3 and 1α,25-dihydroxy-16,23E-diene vitamin D3 : Separation of genomic and nongenomic vitamin D activities. In: Bioorganic and Medicinal Chemistry. 1998 ; Vol. 6, No. 11. pp. 2051-2059.
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