The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1 H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
Open accessAbstract
A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
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Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic.
Masferrer, J. L., Zweifel, B. S., Manning, P. T., Hauser, S. D., Leahy, K. M., Smith, W. G., Isakson, P. C., & Seibert, K. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.8.3228 · Cited by 1,310
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Cited by
The Many Roles for Fluorine in Medicinal Chemistry
Hagmann, W. K. (2008) · Journal of Medicinal Chemistry · doi:10.1021/jm800219f · Cited by 3,578
Ecotoxicology of human pharmaceuticals
Fent, K., Weston, A. A., & Caminada, D. (2006) · Aquatic Toxicology · doi:10.1016/j.aquatox.2005.09.009 · Cited by 3,223
Vane, J. R., Bakhle, Y. S., & Botting, R. M. (1998) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.38.1.97 · Cited by 2,734
McAdam, B. F., Catella-Lawson, F., Mardini, I. A., Kapoor, S., Lawson, J. A., & FitzGerald, G. A. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.1.272 · Cited by 1,305
The Methylation Effect in Medicinal Chemistry
Barreiro, E. J., Kümmerle, A. E., & Fraga, C. A. M. (2011) · Chemical Reviews · doi:10.1021/cr200060g · Cited by 1,017
Metadata
- Authors
- Penning, T. D., Talley, J. J., Bertenshaw, S. R., Carter, J. S., Collins, P. W., Docter, S., Graneto, M. J., Lee, L. F., Malecha, J. W., Miyashiro, J. M., Rogers, R. S., Rogier, D. J., Yu, S. S., Anderson, G. D., Burton, E. G., Cogburn, J. N., Gregory, S. A., Koboldt, C. M., Perkins, W. E., Seibert, K., Veenhuizen, A. W., Zhang, Y. Y., & Isakson, P. C.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-04-01
- Volume
- 40
- Issue
- 9
- Pages
- 1347-1365
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2033498682
- Cited by
- 1,965
- References
- 1
- FWCI
- 47.31
- Type
- journal article
- Language
- en
- Open access
- green
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