Synthesis and biological activity of 3′-alkyl- and 3′-alkenyl-3′-dephenyldocetaxels

Iwao Ojima*, Olivier Duclos, Scott D. Kuduk, Chung-Ming Sun, John C. Slater, François Lavelle, Jean M. Veith, Ralph J. Bernacki

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

3-Alkyl- and 3′-alkenyl-3′-dephenyldocetaxels are synthesized from 10-deacetylbaccatin III based on the β-lactam synthon method in good yields. The cytotoxicity of the new taxoids are evaluated against different human tumor cell lines and their ability to inhibit the microtubules disassembly examined. The 3′-isobutenyl, 3′-crotyl, and 3′-isobutyl analogs possess very strong cytotoxicity as well as antitumor activity in vivo. 3′-Isobutenyl- as well as 3′-crotyl-3′-dephenyl-10-acetyldocetaxel shows ca. 20 times stronger activity against an adriamycin-resistant human breast cancer cell line (MCF7-R) than those o docetaxel and paclitaxel.

Original languageEnglish
Pages (from-to)2631-2634
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume4
Issue number21
DOIs
StatePublished - 10 Nov 1994

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