Inhibition of human cytomegalovirus protease by enedione derivatives of thieno[2,3-d]oxazinones through a novel dual acylation/alkylation mechanism

Enedione derivatives of thieno[2,3-d]oxazinones are nanomolar inhibitors of CMV protease which act through a novel dual acylation of the catalytic serine and alkylation of the protease cysteine 161 via a Michael addition to the enedione moiety of the inhibitor. Enedione derivatives of thieno[2,3-d]o...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1999-02, Vol.9 (3), p.449-452
Main Authors: Pinto, Ivan L., Jarvest, Richard L., Clarke, Brian, Dabrowski, Christine E., Fenwick, Ashley, Gorczyca, Michele M, Jennings, L.John, Lavery, Patrick, Sternberg, Edmund J, Tew, David G., West, Andrew
Format: Article
Language:English
Subjects:
Acylation
Alkylation
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Biological and medical sciences
Cell Survival - drug effects
Medical sciences
Models, Molecular
Oxazines - chemistry
Oxazines - pharmacology
Pharmacology. Drug treatments
Serine Endopeptidases - drug effects
Serine Proteinase Inhibitors - chemistry
Serine Proteinase Inhibitors - pharmacology
Spectrometry, Mass, Fast Atom Bombardment
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
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Summary:Enedione derivatives of thieno[2,3-d]oxazinones are nanomolar inhibitors of CMV protease which act through a novel dual acylation of the catalytic serine and alkylation of the protease cysteine 161 via a Michael addition to the enedione moiety of the inhibitor. Enedione derivatives of thieno[2,3-d]oxazinones are nanomolar inhibitors of CMV protease which act through a novel dual acylation of the catalytic serine and alkylation of the protease cysteine 161 via a Michael addition to the enedione moiety of the inhibitor.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00005-0