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Novel 2-aminopyrimidine carbamates as potent and orally active inhibitors of Lck: synthesis, SAR, and in vivo antiinflammatory activity.

Abstract：

:The lymphocyte-specific kinase (Lck) is a cytoplasmic tyrosine kinase of the Src family expressed in T cells and NK cells. Genetic evidence in both mice and humans demonstrates that Lck kinase activity is critical for signaling mediated by the T cell receptor (TCR), which leads to normal T cell development and activation. A small molecule inhibitor of Lck is expected to be useful in the treatment of T cell-mediated autoimmune and inflammatory disorders and/or organ transplant rejection. In this paper, we describe the synthesis, structure-activity relationships, and pharmacological characterization of 2-aminopyrimidine carbamates, a new class of compounds with potent and selective inhibition of Lck. The most promising compound of this series, 2,6-dimethylphenyl 2-((3,5-bis(methyloxy)-4-((3-(4-methyl-1-piperazinyl)propyl)oxy)phenyl)amino)-4-pyrimidinyl(2,4-bis(methyloxy)phenyl)carbamate (43) exhibits good activity when evaluated in in vitro assays and in an in vivo model of T cell activation.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Martin MW,Newcomb J,Nunes JJ,McGowan DC,Armistead DM,Boucher C,Buchanan JL,Buckner W,Chai L,Elbaum D,Epstein LF,Faust T,Flynn S,Gallant P,Gore A,Gu Y,Hsieh F,Huang X,Lee JH,Metz D,Middleton S,Mohn D,Morgenster

doi

10.1021/jm060435i

subject

Has Abstract

pub_date

2006-08-10 00:00:00

pages

4981-91

issue

16

eissn

0022-2623

issn

1520-4804

journal_volume

49

pub_type

杂志文章

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