Structure–activity relationships study at the 3′- N position of paclitaxel. part 2: synthesis and biological evaluation of 3′- N-thiourea- and 3′- N-thiocarbamate-bearing paclitaxel analogues

The syntheses and preliminary biological evaluation of 3′- N-thiocarbamate- and 3′- N-thiourea-bearing paclitaxel analogues, 4a–f and 5a–e, are described. 3′- N-thiocarbamates 4a–e were found to be more potent than paclitaxel in both the tubulin polymerization assay and the in vitro cytotoxicity ass...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-06, Vol.10 (12), p.1327-1331
Main Authors: Xue, May, Long, Byron H, Fairchild, Craig, Johnston, Kathy, Rose, William C, Kadow, John F, Vyas, Dolatrai M, Chen, Shu-Hui
Format: Article
Language:English
Subjects:
Antineoplastic agents
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
General aspects
Medical sciences
Paclitaxel - analogs & derivatives
Paclitaxel - chemical synthesis
Paclitaxel - chemistry
Paclitaxel - pharmacology
Pharmacology. Drug treatments
Structure-Activity Relationship
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Summary:The syntheses and preliminary biological evaluation of 3′- N-thiocarbamate- and 3′- N-thiourea-bearing paclitaxel analogues, 4a–f and 5a–e, are described. 3′- N-thiocarbamates 4a–e were found to be more potent than paclitaxel in both the tubulin polymerization assay and the in vitro cytotoxicity assay. Several derivatives of this class such as 4c, 4d, and 4e also exhibited some in vivo activity.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(00)00242-0