Antineoplastic agents. 595. structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer1

George Pettit, Noeleen Melody, Frank Hempenstall, Jean Chapuis, Thomas L. Groy, Lee Williams

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

The lupane-type triterpene betulin (1) has been subjected to a series of structural modifications for the purpose of evaluating resultant cancer cell growth inhibitory activity. The reaction sequence 7 11 12 was especially noteworthy in providing a betulin-derived amine dimer. Other unexpected synthetic results included the 11 and 13/1417 conversions, which yielded an imidazo derivative. X-ray crystal structures of dimer 12 and intermediate 25 are reported. All of the betulin modifications were examined for anticancer activity against the P388 murine and human cell lines. Significant cancer cell growth inhibition was found for 4, 8, 9, 15/16, 19, 20, 24, and 26, which further defines the utility of the betulin scaffold.

Original languageEnglish (US)
Pages (from-to)863-872
Number of pages10
JournalJournal of Natural Products
Volume77
Issue number4
DOIs
StatePublished - Apr 25 2014

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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