Journal of medicinal chemistry

Cytotoxic 1, 2-dialkynylimidazole-based aza-enediynes: Aza-Bergman rearrangement rates do not predict cytotoxicity

C Laroche, J Li, SM Kerwin

Index: Laroche, Christophe; Li, Jing; Kerwin, Sean M. Journal of Medicinal Chemistry, 2011 , vol. 54, # 14 p. 5059 - 5069

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Citation Number: 10

Abstract

A new class of potential antitumor agents inspired by the enediyne antitumor antibiotics has been synthesized: the 1, 2-dialkynylimidazoles. The aza-Bergman rearrangement of these 1, 2-dialkynylimidazoles has been investigated theoretically at the B3LYP/6-31G (d, p) level and experimentally by measuring the kinetics of rearrangement in 1, 4-cyclohexadiene. There is a good correlation between the theoretical and experimental results; subtle ...