Paper
Syntheses and structure-activity relationships of taxoids derived from 14β-hydroxy-10-deacetylbaccatin III
Published Jan 31, 1997 · I. Ojima, J. C. Slater, S. Kuduk
Journal of Medicinal Chemistry
101
Citations
0
Influential Citations
Abstract
A series of new taxoids derived from 14β-hydroxy-10-deacetylbaccatin III was synthesized by means of the β-lactam synthon method. Most of the new taxoids thus synthesized possess excellent cytotoxicity against human ovarian (A121), non-small-cell lung (A549), colon (HT-29), and breast (MCF-7) cancer cell lines, and several of these taxoids show subnanomolar IC50 values which are severalfold to 1 order of magnitude better than those of paclitaxel and docetaxel. Modifications at the 3‘- and 3‘-N-positions exert marked effects on the activity. For the substituents at C-3‘, the cytotoxicity decreases in the order 2-furyl ∼ 2-methyl-1-propenyl ≥ 2-methylpropyl > (E)-1-propenyl ≥ n-propyl > phenyl ≫ 2,2-dimethylpropyl. For the 3‘-N substituents, the activity decreases in the order t-BuOCO > Ph > n-hexanoyl. A significant increase in the cytotoxicity against the doxorubicin-resistant human breast cancer cell line MCF7-R that expresses the multidrug resistance (MDR) phenotype is observed by the proper modificatio...
Highly CitedNew taxoids derived from 14-hydroxy-10-deacetylbaccatin III show excellent cytotoxicity against various cancer cell lines, with subnanomolar IC50 values and potential for use in cancer therapy.
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