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Tri- and Tetrasubstituted Pyridinylimidazoles as Covalent Inhibitors of c-Jun N-Terminal Kinase 3.

Abstract：

:The concept of covalent inhibition of c-Jun N-terminal kinase 3 (JNK3) was successfully transferred to our well validated pyridinylimidazole scaffold varying several structural features in order to deduce crucial structure-activity relationships. Joint targeting of the hydrophobic region I and methylation of imidazole-N1 position increased the activity and reduced the number of off-targets. The most promising covalent inhibitor, the tetrasubstituted imidazole 3-acrylamido-N-(4-((4-(4-(4-fluorophenyl)-1-methyl-2-(methylthio)-1H-imidazol-5-yl)pyridin-2-yl)amino)phenyl)benzamide (7) inhibits the JNK3 in the subnanomolar range (IC50 = 0.3 nM), shows high metabolic stability in human liver microsomes, and displays excellent selectivity in a screening against a panel of 410 kinases. Covalent bond formation to Cys-154 was confirmed by incubation of the inhibitors with wild-type JNK3 and JNK3-C154A mutant followed by mass spectrometry.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Muth F,El-Gokha A,Ansideri F,Eitel M,Döring E,Sievers-Engler A,Lange A,Boeckler FM,Lämmerhofer M,Koch P,Laufer SA

doi

10.1021/acs.jmedchem.6b01180

subject

Has Abstract

pub_date

2017-01-26 00:00:00

pages

594-607

issue

2

eissn

0022-2623

issn

1520-4804

journal_volume

60

pub_type

杂志文章

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