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Photochemical preparation of a pyridone containing tetracycle: A jak protein kinase inhibitor

Thompson, James E., Cubbon, Rose M., Cummings, Richard T., Wicker, Linda S., Frankshun, Robert, Cunningham, Barry R., Cameron, Patricia M., Meinke, Peter T., Liverton, Nigel, Weng, Youmin, DeMartino, Julie A.·2002·Bioorganic & Medicinal Chemistry Letters
DOI 10.1016/s0960-894x(02)00106-3
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Abstract

Jak3 is a protein tyrosine kinase that is associated with the shared gamma chain of receptors for cytokines IL2, IL4, IL7, IL9, and IL13. We have discovered that a pyridone-containing tetracycle (6) may be prepared from trisubstituted imidazole (5) in high yield by irradiation with >350 nm light. Compound 6 inhibits Jak3 with K(I)=5 nM; it also inhibits Jak family members Tyk2 and Jak2 with IC(50)=1 nM and murine Jak1with IC(50)=15 nM. Compound 6 was tested as an inhibitor of 21 other protein kinases; it inhibited these kinases with IC(50)s ranging from 130 nM to >10 microM. Compound 6 also blocks IL2 and IL4 dependent proliferation of CTLL cells and inhibits the phosphorylation of STAT5 (an in vivo substrate of the Jak family) as measured by Western blotting.

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Metadata

Authors
Thompson, J. E., Cubbon, R. M., Cummings, R. T., Wicker, L. S., Frankshun, R., Cunningham, B. R., Cameron, P. M., Meinke, P. T., Liverton, N., Weng, Y., & DeMartino, J. A.
Venue
Bioorganic & Medicinal Chemistry Letters
Publisher
Elsevier BV
Published
2002-04
Volume
12
Issue
8
Pages
1219-1223
ISSN
0960-894X
DOI
10.1016/s0960-894x(02)00106-3
Cited by
234
References
1
Language
en
Licence

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CoChat. (2026). Citation check: Photochemical preparation of a pyridone containing tetracycle: A jak protein kinase inhibitor. https://app.cochat.ai/papers/10.1016/s0960-894x(02)00106-3
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Thompson, J. E., Cubbon, R. M., Cummings, R. T., Wicker, L. S., Frankshun, R., Cunningham, B. R., Cameron, P. M., Meinke, P. T., Liverton, N., Weng, Y., & DeMartino, J. A. (2002). Photochemical preparation of a pyridone containing tetracycle: A jak protein kinase inhibitor. Bioorganic & Medicinal Chemistry Letters. https://doi.org/10.1016/s0960-894x(02)00106-3