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.
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Authors | Frédéric Liéby-Muller, Frédéric Marion, Philippe Schmitt, Jean-Philippe Annereau, Anna Kruczynski, Nicolas Guilbaud, Christian Bailly |
Journal | Bioorganic & medicinal chemistry letters
(Bioorg Med Chem Lett)
Vol. 25
Issue 2
Pg. 184-7
(Jan 15 2015)
ISSN: 1464-3405 [Electronic] England |
PMID | 25499434
(Publication Type: Journal Article)
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Copyright | Copyright © 2014 Elsevier Ltd. All rights reserved. |
Chemical References |
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Topics |
- Alkaloids
(chemical synthesis, pharmacology)
- Cell Line, Tumor
- Cell Proliferation
(drug effects, physiology)
- Drug Evaluation, Preclinical
(methods)
- Humans
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