Semisynthesis and biological evaluation of a novel D-seco docetaxel analogue.
[reaction: see text] A 4-methyl-5-oxo docetaxel analogue has been prepared starting from 10-deacetylbaccatin III. This new D-seco docetaxel analogue is slightly less potent than docetaxel at microtubule stabilization in vitro and has about 1/1000th the cytotoxicity of docetaxel. The lack of improved activity for this compound compared to other D-modified taxoids confirms that a C-5 oxygen atom is not required for biological activity.
Thoret
Sylviane
S
Institut de Chimie des Substances Naturelles-CNRS, Gif sur Yvette, France.
Guéritte
Françoise
F
Guénard
Daniel
D
Dubois
Joëlle
J
D000077143:Docetaxel; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D043823:Taxoids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D043823:Taxoids; D000077143:Docetaxel