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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Synthesis and structure-activity relationships of novel 2',2'-difluoro analogues of docetaxel.

To investigate the role of the 2'-hydroxy group at the C-13 side chain of docetaxel in the antitumor activity, we prepared several 2',2'-difluoro derivatives of docetaxel and evaluated their cytotoxicity against mouse leukemia and human tumor cell lines and their microtubule disassembly-inhibitory activity. These analogues were prepared by esterification of protected 10-deacetylbaccatin III (21) with appropriate alpha, alpha-difluorinated carboxylic acids (Charts 1 and 2). Among these 2',2'-difluorodocetaxel derivatives, 2',2'-difluorodocetaxel (23b) was approximately 3-10 times as active as 2'-fluorodocetaxel (29a) in terms of cytotoxicity. In addition, the 3'-(2-furyl) (23h) and 3'-(2-pyrrolyl) (23p) analogues showed activity comparable or superior to that of docetaxel (2).[1]


  1. Synthesis and structure-activity relationships of novel 2',2'-difluoro analogues of docetaxel. Uoto, K., Ohsuki, S., Takenoshita, H., Ishiyama, T., Iimura, S., Hirota, Y., Mitsui, I., Terasawa, H., Soga, T. Chem. Pharm. Bull. (1997) [Pubmed]
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