Synthesis and biological evaluation of novel C-4 aziridine-bearing paclitaxel (taxol) analogs.
Three novel C-4 aziridine-bearing paclitaxel analogs, 3-5, have been synthesized during the course of our continuing effort at C-4 modification. The key step in the synthesis is the aziridine ring formation at the C-4 position via an intramolecular Mitsunobu reaction. The syntheses and the biological evaluation of these C-4 aziridine-containing derivatives are herein discussed.
Chen
S H
SH
Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut 06492-7660, USA.
Fairchild
C
C
Long
B H
BH
D001388:Aziridines / Q000737:chemistry*; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000737:chemistry
D001388:Aziridines; D014404:Tubulin; C033132:aziridine; D017239:Paclitaxel