Synthesis and bioactivity of 2,4-diacyl analogues of paclitaxel

The 2,4-diacyl paclitaxel analogues 8a– 8r were prepared from paclitaxel by acylation of 4-deacetyl-2-debenzoylpaclitaxel 1,2-carbonate ( 3 ) followed either by hydrolysis of the carbonate and acylation or by direct treatment of the carbonate with an aryllithium. Some of the resulting derivatives sh...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2001, Vol.9 (1), p.171-178
Main Authors: Chordia, Mahendra D, Yuan, Haiqing, Jagtap, Prakash G, Kadow, John F, Long, Byron H, Fairchild, Craig R, Johnston, Kathy A, Kingston, David G.I
Format: Article
Language:English
Subjects:
Antineoplastic agents
Antineoplastic Agents, Phytogenic - chemical synthesis
Biological and medical sciences
Cell Survival
General aspects
Humans
Medical sciences
Microtubule-Associated Proteins - biosynthesis
Molecular Structure
Paclitaxel - analogs & derivatives
Paclitaxel - chemical synthesis
Paclitaxel - pharmacology
Pharmacology. Drug treatments
Tumor Cells, Cultured - drug effects
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Summary:The 2,4-diacyl paclitaxel analogues 8a– 8r were prepared from paclitaxel by acylation of 4-deacetyl-2-debenzoylpaclitaxel 1,2-carbonate ( 3 ) followed either by hydrolysis of the carbonate and acylation or by direct treatment of the carbonate with an aryllithium. Some of the resulting derivatives showed significantly improved tubulin assembly activity and cytotoxicity as compared with paclitaxel; in some cases this improvement was especially significant for paclitaxel-resistant cell lines.
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(00)00233-9