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

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 (e.g., CDDO and bardoxolone methyl) and tricycles (e.g., TBE-31). Among monocyclic cyanoenones, 1 is a highly reactive Michael acceptor with thiol nucleophiles. Furthermore, an important feature of 1 is that its Michael addition is reversible. For the inhibition of NO production, 1 shows the highest potency. Notably, its potency is about three times higher than CDDO, whose methyl ester (bardoxolone methyl) is presently in phase III clinical trials. For the induction of NQO1, 1 also demonstrated the highest potency. These results suggest that the reactivity of these Michael acceptors is closely related to their biological potency. Interestingly, in LPS-stimulated macrophages, 1 causes apoptosis and inhibits secretion of TNF-α and IL-1β with potencies that are higher than those of bardoxolone methyl and TBE-31.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Zheng S,Santosh Laxmi YR,David E,Dinkova-Kostova AT,Shiavoni KH,Ren Y,Zheng Y,Trevino I,Bumeister R,Ojima I,Wigley WC,Bliska JB,Mierke DF,Honda T

doi

10.1021/jm3003922

subject

Has Abstract

pub_date

2012-05-24 00:00:00

pages

4837-46

issue

10

eissn

0022-2623

issn

1520-4804

journal_volume

55

pub_type

杂志文章

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