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Design and Synthesis of Celecoxib and Rofecoxib Analogues as Selective Cyclooxygenase-2 (COX-2) Inhibitors: Replacement of Sulfonamide and Methylsulfonyl Pharmacophores by an Azido Bioisostere
Open accessAbstract
Celecoxib (13) and rofecoxib (17) analogues, in which the respective SO2NH2 and SO2Me hydrogen-bonding pharmacophores were replaced by a dipolar azido bioisosteric substituent, were investigated. Molecular modeling (docking) studies showed that the azido substituent of these two analogues (13, 17) was inserted deep into the secondary pocket of the human COX-2 binding site where it undergoes electrostatic interaction with Arg(513). The azido analogue of rofecoxib (17), the most potent and selective inhibitor of COX-2 (COX-1 IC(50) = 159.7 microM; COX-2 IC(50) = 0.196 microM; COX-2 selectivity index = 812), exhibited good oral antiinflammatory and analgesic activities.
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Cited by
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Fustero, S., Sánchez-Roselló, M., Barrio, P., & Simón-Fuentes, A. (2011) · Chemical Reviews · doi:10.1021/cr2000459 · Cited by 1,155
Prostaglandin E2 synthesis and secretion: The role of PGE2 synthases
Park, J. Y., Pillinger, M. H., & Abramson, S. B. (2006) · Clinical Immunology · doi:10.1016/j.clim.2006.01.016 · Cited by 793
Rao, P., & Knaus, E. E. (2008) · Journal of Pharmacy & Pharmaceutical Sciences · doi:10.18433/j3t886 · Cited by 773
Self-citationDistinct functions of COX-1 and COX-2
Morita, I. (2002) · Prostaglandins & Other Lipid Mediators · doi:10.1016/s0090-6980(02)00029-1 · Cited by 462
Murias, M., Handler, N., Erker, T., Pleban, K., Ecker, G., Saiko, P., Szekeres, T., & Jäger, W. (2004) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2004.08.008 · Cited by 288
Metadata
- Authors
- Habeeb, A. G., Praveen Rao, P. N., & Knaus, E. E.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-08-01
- Volume
- 44
- Issue
- 18
- Pages
- 3039-3042
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2083375837
- Cited by
- 215
- References
- 0
- FWCI
- 2.79
- Type
- journal article
- Language
- en
- Open access
- green
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