Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives

Eur J Med Chem. 2011 Jun;46(6):2490-502. doi: 10.1016/j.ejmech.2011.03.038. Epub 2011 Mar 25.

Abstract

Based on structural modifications of the natural 23-hydroxybetulinic acid, a series of novel its derivatives had been synthesized. The new compounds were screened for in vitro antiproliferative activity against cancer cell lines HeLa, MCF-7, HepG2, B16 and A375 using doxorubicin as a reference. The vast majority of derivatives had exhibited potent tumor growth inhibitory activity than original compound. The derivatives 4, 5, 7, 20, 23, 26, 43 and 44 with IC50 values lower than 10 μM on all tested cell lines were regarded as the most promising compounds. The structure-activity relationships of 23-hydroxybetulinic acid derivatives were also discussed in the present investigations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*
  • Tumor Cells, Cultured

Substances

  • 23-hydroxybetulinic acid
  • Antineoplastic Agents
  • Triterpenes