Synthesis and biological activity of novel 3′-trifluoromethyl taxoids

Second generation taxoids possessing a trifluoromethyl moiety in place of the 3′-phenyl group are synthesized by means of the β- Lactam Synthon Method. The in vitro cytotoxicities of these new taxoids are evaluated against several different human cancer cell lines and found to exhibit greatly enhanc...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1997-01, Vol.7 (2), p.133-138
Main Authors: Ojima, Iwao, Slater, John C., Pera, Paula, Veith, Jean M., Abouabdellah, Ahmed, Bégué, Jean-Pierre, Bernacki, Ralph J.
Format: Article
Language:English
Subjects:
Antineoplastic agents
Biological and medical sciences
General aspects
Medical sciences
Pharmacology. Drug treatments
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Summary:Second generation taxoids possessing a trifluoromethyl moiety in place of the 3′-phenyl group are synthesized by means of the β- Lactam Synthon Method. The in vitro cytotoxicities of these new taxoids are evaluated against several different human cancer cell lines and found to exhibit greatly enhanced activities as compared to those of paclitaxel and docetaxel. The activity enhancement is most remarkable against a drug-resistant breast cancer cell line, MCF7-R, expressing MDR phenotype. A series 3′-CF 3-taxoids, synthesized via a kinetic resolution of racemic β-lactam with baccatins, exhibit excellent activity against a range of human cancer cell lines, in particular, drug-resistant breast cancer cells.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(96)00595-1