Syntheses of immunomodulating androstanes and stigmastanes: comparison of their TNF-alpha inhibitory activity

Bioorg Med Chem. 2007 Dec 15;15(24):7538-44. doi: 10.1016/j.bmc.2007.09.012. Epub 2007 Sep 14.

Abstract

In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-alpha production by macrophages. A preliminary qualitative structure-activity relationship was established.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstanes / chemical synthesis*
  • Androstanes / chemistry
  • Androstanes / pharmacology*
  • Animals
  • Cell Line
  • Cholestanes / chemical synthesis*
  • Cholestanes / chemistry
  • Cholestanes / pharmacology*
  • Dehydroepiandrosterone / chemistry
  • Drug Evaluation, Preclinical
  • Immunologic Factors / chemical synthesis
  • Immunologic Factors / chemistry
  • Immunologic Factors / pharmacology
  • Mice
  • Molecular Structure
  • Stigmasterol / chemistry
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*

Substances

  • Androstanes
  • Cholestanes
  • Immunologic Factors
  • Tumor Necrosis Factor-alpha
  • Dehydroepiandrosterone
  • Stigmasterol