First total synthesis of phenylpyridine analogues of the antimitotic rhazinilam

E Pasquinet, P Rocca, S Richalot…

Index: Pasquinet; Rocca; Richalot; Gueritte; Guenard; Godard; Marsais; Queguiner Journal of Organic Chemistry, 2001 , vol. 66, # 8 p. 2654 - 2661

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Citation Number: 26

Abstract

The first synthesis of phenylpyridine analogues of rhazinilam and evaluation of these new structures as inhibitors of microtubule disassembly by interaction with tubulin are described. The synthesis is based on such key steps as picolinic metalation, hetero-ring cross-coupling and reduction of an acetyl group to an ethyl group. Elaboration of a quaternary picolinic carbon is one of the challenges of the synthesis. Biological evaluation of compounds ...