2. Academic Validation
  3. Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs

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

  • Bioorg Med Chem Lett. 2015 Jan 15;25(2):184-7. doi: 10.1016/j.bmcl.2014.11.086.
Frédéric Liéby-Muller 1,  Frédéric Marion 2,  Philippe Schmitt 2,  Jean-Philippe Annereau 2,  Anna Kruczynski 2,  Nicolas Guilbaud 2,  Christian Bailly 2
Affiliations

Affiliations

  • 1 Institut de Recherche Pierre Fabre, CRDPF/CROE, 3 avenue Hubert Curien, BP 13562, 31035 Toulouse Cedex 1, France. Electronic address: frederic.lieby.muller@pierre-fabre.com.
  • 2 Institut de Recherche Pierre Fabre, CRDPF/CROE, 3 avenue Hubert Curien, BP 13562, 31035 Toulouse Cedex 1, France.
PMID: 25499434 DOI: 10.1016/j.bmcl.2014.11.086
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.

Keywords

(−)-Cryptopleurine; Cytotoxicity; Phenanthroquinolizidine alkaloid.

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