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Discovery of Selective, Orally Bioavailable Pyrazolopyridine Inhibitors of Protein Kinase Cθ (PKCθ) That Ameliorate Symptoms of Experimental Autoimmune Encephalomyelitis.


ABSTRACT: PKCθ plays an important role in T cell biology and is a validated target for a number of disease states. A series of potent and selective PKCθ inhibitors were designed and synthesized starting from a HTS hit compound. Cell activity, while initially a challenge to achieve, was built into the series by transforming the nitrile unit of the scaffold into a primary amine, the latter predicted to form a new hydrogen bond to Asp508 near the entrance of the ATP binding site of PKCθ. Significant improvements in physiochemical parameters were observed on introduction of an oxetane group proximal to a primary amine leading to compound 22, which demonstrated a reduction of symptoms in a mouse model of multiple sclerosis.

SUBMITTER: Collier PN 

PROVIDER: S-EPMC6693473 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Discovery of Selective, Orally Bioavailable Pyrazolopyridine Inhibitors of Protein Kinase Cθ (PKCθ) That Ameliorate Symptoms of Experimental Autoimmune Encephalomyelitis.

Collier Philip N PN   Twin Heather C HC   Knegtel Ronald M A RMA   Boyall Dean D   Brenchley Guy G   Davis Christopher J CJ   Keily Shazia S   Mak Chau C   Miller Andrew A   Pierard Françoise F   Settimo Luca L   Bolton Clare M CM   Chiu Peter P   Curnock Adam A   Doyle Elisabeth E   Tanner Adam J AJ   Jimenez Juan-Miguel JM  

ACS medicinal chemistry letters 20190627 8


PKCθ plays an important role in T cell biology and is a validated target for a number of disease states. A series of potent and selective PKCθ inhibitors were designed and synthesized starting from a HTS hit compound. Cell activity, while initially a challenge to achieve, was built into the series by transforming the nitrile unit of the scaffold into a primary amine, the latter predicted to form a new hydrogen bond to Asp508 near the entrance of the ATP binding site of PKCθ. Significant improvem  ...[more]

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