Design and synthesis of simplified taxol analogs based on the T-Taxol bioactive conformation

…, JP Snyder, H Hu, K Mukherjee, C Slebodnick…

Index: Zhao, Jielu; Bane, Susan; Snyder, James P.; Hu, Haipeng; Mukherjee, Kamalika; Slebodnick, Carla; Kingston, David G.I. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 24 p. 7664 - 7678

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Citation Number: 14

Abstract

A series of compounds designed to adopt a conformation similar to the tubulin-binding T- Taxol conformation of the anticancer drug paclitaxel has been synthesized. Both the internally bridged analogs 37–39, 41 and the open-chain analogs 27–29 and 43 were prepared. The bridged analogs 37–39 and 41 were synthesized by Grubbs' metatheses of compounds 30–32 and 33, which, in turn, were prepared by coupling β-lactams 24–26 ...