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Elaboration of Simplified Vinca Alkaloids and Phomopsin Hybrids
Author(s) -
Ngo Quoc Anh,
Roussi Fanny,
Thoret Sylviane,
Guéritte Françoise
Publication year - 2010
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2009.00922.x
Subject(s) - vindoline , vinca , moiety , chemistry , tubulin , stereochemistry , combinatorial chemistry , organic chemistry , microtubule , vinblastine , biology , pharmacology , genetics , chemotherapy , microbiology and biotechnology
Nine simplified vinca alkaloids and phomospin A hybrids, in which vindoline moiety has been replaced by a simpler scaffold, have been elaborated to evaluate their activity on the inhibition of tubulin polymerization. This article deals with the synthesis of various simplified vinca alkaloids, using a stereoselective coupling of catharantine with reactive aromatic compounds and methanol as well as their subsequent condensation with a large peptide chain mimicking those of phomopsin A. Biological evaluation and molecular modeling studies are also reported.