Synthesis, chemical reactivity as Michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective …

…, AT Dinkova-Kostova, KH Shiavoni, Y Ren…

Index: Zheng, Suqing; Santosh Laxmi; David, Emilie; Dinkova-Kostova, Albena T.; Shiavoni, Katherine H.; Ren, Yanqing; Zheng, Ying; Trevino, Isaac; Bumeister, Ronald; Ojima, Iwao; Wigley, W. Christian; Bliska, James B.; Mierke, Dale F.; Honda, Tadashi Journal of Medicinal Chemistry, 2012 , vol. 55, # 10 p. 4837 - 4846

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Citation Number: 32

Abstract

Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (eg, CDDO and bardoxolone methyl) and tricycles (eg, TBE-31). Among monocyclic cyanoenones, 1 is a highly reactive Michael acceptor with thiol nucleophiles. Furthermore, ...