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  • Title: Synthesis and biological activity of fluorinated combretastatin analogues.
    Author: Alloatti D, Giannini G, Cabri W, Lustrati I, Marzi M, Ciacci A, Gallo G, Tinti MO, Marcellini M, Riccioni T, Guglielmi MB, Carminati P, Pisano C.
    Journal: J Med Chem; 2008 May 08; 51(9):2708-21. PubMed ID: 18396857.
    Abstract:
    With the aim of understanding the influence of fluorine on the double bond of the cis-stilbene moiety of combretastatin derivatives and encouraged by a preliminary molecular modeling study showing a different biological environment on the interaction site with tubulin, we prepared, through various synthetic approaches, a small library of compounds in which one or both of the olefinic hydrogens were replaced with fluorine. X-ray analysis on the difluoro-CA-4 analogue demonstrated that the spatial arrangement of the molecule was not modified, compared to its nonfluorinated counterpart. SAR analysis confirmed the importance of the cis-stereochemistry of the stilbene scaffold. Nevertheless, some unpredicted results were observed on a few trans-fluorinated derivatives. The position of a fluorine atom on the double bond may affect the inhibition of tubulin polymerization and cytotoxic activity of these compounds.
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