Organic & Biomolecular Chemistry 2013-09-21

Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline.

Emerson Giovanelli, Lionel Moisan, Sébastien Comesse, Sébastien Leroux, Bernard Rousseau, Paul Hellier, Marc Nicolas, Eric Doris

Index: Org. Biomol. Chem. 11(35) , 5885-91, (2013)

Full Text: HTML

Abstract

The syntheses of 20,20-difluorocatharanthine and congeners, starting from the naturally occurring catharanthine, are reported. The fluorinated catharanthine analogues were investigated as potential precursors to dimeric Vinca alkaloids of the vinflunine family. However, the biomimetic coupling of the fluorinated catharanthine derivatives with vindoline led to unexpected alkaloid structures, the formation of which was rationalized.

Related Compounds

  • Catharanthine
  • Vindoline

Related Articles:

Catharanthine dilates small mesenteric arteries and decreases heart rate and cardiac contractility by inhibition of voltage-operated calcium channels on vascular smooth muscle cells and cardiomyocytes.

2013-06-01

[J. Pharmacol. Exp. Ther. 345(3) , 383-92, (2013)]

The leaf epidermome of Catharanthus roseus reveals its biochemical specialization.

2008-03-01

[Plant Cell 20(3) , 524-42, (2008)]

Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry.

2011-10-01

[J. Sep. Sci. 34 , 2885-2892, (2011)]

Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

2010-11-15

[Bioorg. Med. Chem. Lett. 20(22) , 6408-10, (2010)]

Synergistic and cytotoxic action of indole alkaloids produced from elicited cell cultures of Catharanthus roseus.

2013-03-01

[Pharm. Biol. 51(3) , 304-10, (2013)]

More Articles...