Synthesis and biological evaluation of antitumour-active betulin derivatives

Bioorg Med Chem. 2010 Feb;18(3):1344-55. doi: 10.1016/j.bmc.2009.12.024. Epub 2009 Dec 23.

Abstract

The reaction of betulinic aldehydes with various carbon nucleophiles gave a series of new betulin derivatives, among them epoxides, glycidic derivatives and beta-hydroxy carbonyl compounds. Subsequent transformations of the beta-hydroxy carbonyls lead to 1,3-diketo- and alpha,beta-unsaturated betulin derivatives. These compounds were assayed for cytotoxicity using 15 human cancer cell lines and a colorimetric SRB-assay. Several compounds revealed significant antitumour activity.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis*
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Triterpenes
  • betulin