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Relevant academic research and scientific papers

Taxol Structure-Activity Relationships: Synthesis and Biological Evaluation of 10-Deoxytaxol

10-Deoxytaxol 2 was prepared from taxol (1) in four steps via the intermediate dienone 5b; the key reaction in the sequence is a Yarovenko reagent-mediated dehydration at the C-10 hydroxyl group.Compound 2 was found to possess comparable antitumor activity with respect to taxol.This confirms that the functional group at C-10 in taxol is not involved in receptor binding.

Relationships between the structure of taxol analogues and their antimitotic activity

A variety of synthetic analogues of taxol, a naturally occurring antitumor diterpene, were examined for their potency to inhibit microtubule disassembly. For some of the compounds, the in vitro cytotoxic properties showed a good correlation with the tubulin assay. This structure-activity relationship study shows that inhibition of microtubule disassembly is quite sensitive to the configuration at C-2' and C-3'. A correlation between the conformation of the side chain at C-13 and the activity is suggested. Of all the compounds examined, one of the most potent in inhibiting microtubule disassembly and in inhibiting murine P388 leukemic cells, N-debenzoyl-N-tert-(butoxycarbonyl)-10-deacetyltaxol, named taxotere, was selected for evaluation as a potential anticancer agent.