Design and efficient synthesis of new stable 1alpha,25-dihydroxy-19-norvitamin D3 analogues containing amide bond

Bioorg Med Chem Lett. 2002 Dec 16;12(24):3533-6. doi: 10.1016/s0960-894x(02)00800-4.

Abstract

The design and synthesis of new 1alpha,25-dihydroxy-19-norvitamin D(3) analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16 was synthesized from Grundmann's ketone. Coupling those parts gave desired 3a-c in good yield. This strategy can be applied in combinatorial chemistry; therefore, those compounds would be applicable as useful tools in the development of new drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Binding Sites
  • Calcitriol / analogs & derivatives*
  • Calcitriol / chemical synthesis*
  • Calcitriol / chemistry
  • Drug Design
  • Models, Molecular
  • Receptors, Calcitriol / chemistry
  • Structure-Activity Relationship

Substances

  • Amides
  • Receptors, Calcitriol
  • 1,25-dihydroxy-19-norvitamin D3
  • Calcitriol