Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors
| Autor: | Pankaj R. Daga, V. Saibaba, Sunil Kumar Singh, V. Ravikumar, Pragathi Hegde, C. Seshagiri Rao, Y. Koteswar Rao, Santosh Rudrawar, Vangoori Akhila |
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| Rok vydání: | 2004 |
| Předmět: |
Male
Molecular model Stereochemistry Clinical Biochemistry Drug Evaluation Preclinical Pharmaceutical Science Biochemistry Sulfone chemistry.chemical_compound In vivo Quinoxalines Drug Discovery Animals Edema Cyclooxygenase Inhibitors Rats Wistar Molecular Biology chemistry.chemical_classification biology Cyclooxygenase 2 Inhibitors Organic Chemistry Biological activity Prodrug Sulfonamide Rats Isoenzymes chemistry Enzyme inhibitor Cyclooxygenase 2 Prostaglandin-Endoperoxide Synthases Pyrazines biology.protein Molecular Medicine Pharmacophore |
| Zdroj: | Bioorganicmedicinal chemistry. 12(8) |
| ISSN: | 0968-0896 |
| Popis: | Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO 2 NH 2 )/methylsulfonyl (SO 2 Me)-phenyl pharmacophores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure–activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. |
| Databáze: | OpenAIRE |
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