A-ring hydroxymethyl 19-nor analogs of the natural hormone 1α,25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation

Mark A. Hatcher, Sara Peleg, Patrick Dolan, Thomas W. Kensler, Amy Sarjeant, Gary H. Posner

Research output: Contribution to journalArticlepeer-review

Abstract

A series 5-8 of 1- and 3-CH2OH 19-nor analogs of the hormone calcitriol (1) has been prepared. Surprisingly, 19-nor 1α-CH2OH analog 5a is more antiproliferative at 100 nM concentration than the corresponding regioisomeric analog 6a with the natural 1α-OH group, and 1α-CH2OH hybrid analog 7a is similar in antiproliferative potency to calcitriol (1) even at low nanomolar concentrations.

Original languageEnglish (US)
Pages (from-to)3964-3976
Number of pages13
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number12
DOIs
StatePublished - Jun 2 2005

Keywords

  • 19-Nor
  • Calcitriol
  • Hydroxymethyl A-ring
  • Novel analogs

ASJC Scopus subject areas

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

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