Bioorganic & Medicinal Chemistry Letters 2011-01-15

Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation.

Ornella Mesenzani, Alberto Massarotti, Mariateresa Giustiniano, Tracey Pirali, Valentina Bevilacqua, Antonio Caldarelli, Pierluigi Canonico, Giovanni Sorba, Ettore Novellino, Armando A Genazzani, Gian Cesare Tron

文献索引：Bioorg. Med. Chem. Lett. 21(2) , 764-8, (2011)

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摘要

In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker.Copyright © 2010 Elsevier Ltd. All rights reserved.