Structure-based design and synthesis of potent benzothiazole inhibitors of interleukin-2 inducible T cell kinase (ITK)
Inhibition of the non-receptor tyrosine kinase ITK, a component of the T-cell receptor signalling cascade, may represent a novel treatment for allergic asthma. Here we report the structure-based optimization of a series of benzothiazole amides that demonstrate sub-nanomolar inhibitory potency agains...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 23; no. 23; pp. 6331 - 6335 |
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| Main Authors | , , , , , , , , , , , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Elsevier Ltd
01.12.2013
Elsevier |
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| Abstract | Inhibition of the non-receptor tyrosine kinase ITK, a component of the T-cell receptor signalling cascade, may represent a novel treatment for allergic asthma. Here we report the structure-based optimization of a series of benzothiazole amides that demonstrate sub-nanomolar inhibitory potency against ITK with good cellular activity and kinase selectivity. We also elucidate the binding mode of these inhibitors by solving the X-ray crystal structures of several inhibitor-ITK complexes. |
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| AbstractList | Inhibition of the non-receptor tyrosine kinase ITK, a component of the T-cell receptor signalling cascade, may represent a novel treatment for allergic asthma. Here we report the structure-based optimization of a series of benzothiazole amides that demonstrate sub-nanomolar inhibitory potency against ITK with good cellular activity and kinase selectivity. We also elucidate the binding mode of these inhibitors by solving the X-ray crystal structures of several inhibitor-ITK complexes. Inhibition of the non-receptor tyrosine kinase ITK, a component of the T-cell receptor signalling cascade, may represent a novel treatment for allergic asthma. Here we report the structure-based optimization of a series of benzothiazole amides that demonstrate sub-nanomolar inhibitory potency against ITK with good cellular activity and kinase selectivity. We also elucidate the binding mode of these inhibitors by solving the X-ray crystal structures of several inhibitor-ITK complexes. (C) 2013 Elsevier Ltd. All rights reserved. |
| Author | Pérez-Fuertes, Yolanda Liimatta, Marya Chen, Yuan Johnson, Adam Lau, Kevin Dines, Jonathon Stein, Daniel B. Kruger, Susanne Heifetz, Alexander Vaidya, Darshan G. Ly, Justin Pei, Zhonghua Eigenbrot, Charles Kraemer, Joachim Shia, Steven Wang, Xiaolu Wu, Lawren C. Burch, Jason D. Ding, Xiao Ortwine, Daniel F. MacKinnon, Colin H. Jaochico, Allan Montalbetti, Christian A.G.N. Maghames, Rosemary Bromidge, Steven M. Krülle, Thomas M. Trani, Giancarlo |
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| Keywords | ITK inhibitor TCR signalling SAR Anti-inflammatory Benzothiazole Asthma TEC KINASES TYROSINE KINASE CRYSTAL-STRUCTURES DISCOVERY INSIGHTS LEAD |
| Language | English |
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| SubjectTerms | amides Animals Anti-inflammatory Asthma Benzothiazole Benzothiazoles - chemical synthesis Benzothiazoles - chemistry Benzothiazoles - pharmacology Chemistry Chemistry, Medicinal Chemistry, Organic Crystallography, X-Ray Drug Design Humans interleukin-2 ITK inhibitor Life Sciences & Biomedicine Mice Models, Molecular Pharmacology & Pharmacy Physical Sciences Protein-Tyrosine Kinases - antagonists & inhibitors Protein-Tyrosine Kinases - chemistry SAR Science & Technology Signal Transduction Structure-Activity Relationship T-lymphocytes TCR signalling tyrosine X-ray diffraction |
| Title | Structure-based design and synthesis of potent benzothiazole inhibitors of interleukin-2 inducible T cell kinase (ITK) |
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