Synthesis of 2-pyridones as tissue factor VIIa inhibitors

2-Pyridones were prepared from 2,6-dibromopyridine via a multi-step synthesis. A variety of chemical transformations, including regioselective nucleophilic addition and selective nitrogen alkylation, afforded the penultimate intermediate 9. A combination of two-dimensional NMR techniques to unequivo...

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Bibliographic Details
Published inTetrahedron Vol. 59; no. 39; pp. 7695 - 7701
Main Authors Parlow, John J, South, Michael S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.09.2003
Elsevier
Subjects
2-pyridones
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tissue factor VIIa
2-pyridones
tissue factor VIIa
SERINE-PROTEASE INHIBITORS
DESIGN
COMPLEX
FACTOR PATHWAY
IN-VITRO EVALUATION
HUMAN-LEUKOCYTE ELASTASE
INDUCED COAGULATION
NONPEPTIDIC INHIBITORS
FACTOR XA INHIBITORS
THROMBIN INHIBITOR
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Summary:2-Pyridones were prepared from 2,6-dibromopyridine via a multi-step synthesis. A variety of chemical transformations, including regioselective nucleophilic addition and selective nitrogen alkylation, afforded the penultimate intermediate 9. A combination of two-dimensional NMR techniques to unequivocally assign the structure of 9 is described. Compound 9 was then used in a Suzuki coupling and further derivatized to afford the targeted tissue Factor VIIa inhibitors. These compounds were tested in several serine protease enzyme assays with biological activity reported. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)01239-0