Synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al with antileukemic activity

J Asian Nat Prod Res. 2012;14(2):141-53. doi: 10.1080/10286020.2011.640774. Epub 2011 Dec 14.

Abstract

An easy and efficient route to partial synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al (1), starting from betulinic acid (2), has been developed (eight steps, 44% overall yield). Structures of all the compounds were determined by spectral studies (IR, (1)H, (13)C NMR, MS, NOESY, COSY, etc.). Compound 1 and the precursors (2, 3, 5, and 7) showed antiproliferative activities against human K562 leukemia, murine WEHI3 leukemia, and murine MEL erythroid progenitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Betulinic Acid
  • Drug Screening Assays, Antitumor
  • Humans
  • K562 Cells
  • Leukemia
  • Mice
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pentacyclic Triterpenes
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • 28-hydroxy-3-oxo-lup-20(29)-en-30-al
  • Antineoplastic Agents, Phytogenic
  • Pentacyclic Triterpenes
  • Triterpenes
  • Betulinic Acid