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

Bioorg Med Chem. 2001 Feb;9(2):403-15. doi: 10.1016/s0968-0896(00)00259-5.

Abstract

A-ring diastereomers of 1alpha,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1alpha,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1alpha,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-1alpha,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1alpha,25-dihydroxyvitamin D3 (1).

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / metabolism
  • Calcitriol / analogs & derivatives
  • Calcitriol / chemical synthesis*
  • Calcitriol / metabolism*
  • Cattle
  • Cell Differentiation / drug effects
  • HL-60 Cells
  • Humans
  • Osteocalcin / drug effects
  • Osteocalcin / genetics
  • Protein Binding
  • Rats
  • Receptors, Calcitriol / metabolism
  • Stereoisomerism
  • Steroid Hydroxylases / drug effects
  • Steroid Hydroxylases / genetics
  • Transcriptional Activation / drug effects
  • Vitamin D-Binding Protein / metabolism

Substances

  • Antineoplastic Agents
  • Receptors, Calcitriol
  • Vitamin D-Binding Protein
  • Osteocalcin
  • Steroid Hydroxylases
  • Calcitriol
  • maxacalcitol