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Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs.

Abstract
(-)-Cryptopleurine 1 is one of the most potent anti-proliferative member of the phenanthroquinolizidine class of alkaloids. We report here the synthesis of (-)-6-O-desmethylcryptopleurine (-)-2 and (-)-6-O-desmethyl-(15R)-hydroxycryptopleurine (-)-4 in their enantiomerically enriched form through a convergent synthetic route, where the chirality is introduced by the use of commercially available (R)-methyl piperidine-2-carboxylate hydrochloride 17. Anti-proliferative activities of these compounds were evaluated on a panel of four cancer cell lines, revealing that compounds (-)-2 and (-)-4 are potent cytotoxic compared to cryptopleurine.
AuthorsFrédéric Liéby-Muller, Frédéric Marion, Philippe Schmitt, Jean-Philippe Annereau, Anna Kruczynski, Nicolas Guilbaud, Christian Bailly
JournalBioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 25 Issue 2 Pg. 184-7 (Jan 15 2015) ISSN: 1464-3405 [Electronic] England
PMID25499434 (Publication Type: Journal Article)
CopyrightCopyright © 2014 Elsevier Ltd. All rights reserved.
Chemical References
  • Alkaloids
  • cryptopleurine
Topics
  • Alkaloids (chemical synthesis, pharmacology)
  • Cell Line, Tumor
  • Cell Proliferation (drug effects, physiology)
  • Drug Evaluation, Preclinical (methods)
  • Humans

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