Deletion of the oxetane ring in docetaxel analogues: synthesis and biological evaluation.
Two new docetaxel analogues have been prepared starting from 10-deacetylbaccatin III. Both derivatives lack the oxetane D-ring but possess the 4alpha-acetoxy group, which is important for biological activity. The influence of a more or less constrained C-ring was evaluated by adding, or not adding, a double bond in this ring. Both compounds were found to be equally less active than docetaxel in biological assays. [reaction: see text]
Deka
Vaishali
V
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Dubois
Joëlle
J
Thoret
Sylviane
S
Guéritte
Françoise
F
Guénard
Daniel
D
D000107:Acetylation; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D000077143:Docetaxel; D004988:Ethers, Cyclic / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D043823:Taxoids / Q000138:chemical synthesis*
D000972:Antineoplastic Agents, Phytogenic; D004988:Ethers, Cyclic; D007202:Indicators and Reagents; D043823:Taxoids; D000077143:Docetaxel; C005287:oxetane