2,935
Views
59
CrossRef citations to date
0
Altmetric
Research Article

3-Methyl-2-phenyl-1-substituted-indole derivatives as indomethacin analogs: design, synthesis and biological evaluation as potential anti-inflammatory and analgesic agents

, &
Pages 318-324 | Received 30 Dec 2014, Accepted 12 Feb 2015, Published online: 23 Mar 2015

References

  • Fletcher BS, Kujubu DA, Perrin DM, Herschman HR. Structure of the mitogen-inducible TIS10 gene and demonstration that the TIS10-encoded protein is a functional prostaglandin G/H synthase. J Biol Chem 1992;267:4338–44
  • Zarghi A, Najafnia L, Daraee B, et al. Synthesis of 2,3-diaryl-1,3-thiazolidine-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors. Bioorg Med Chem Lett 2007;17:5634–7
  • Zebardast T, Zarghi A, Daraie B, et al. Design and synthesis of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors. Bioorg Med Chem Lett 2009;19:3162–5
  • Smith WL, Dewitt DL. Prostaglandin endoperoxide H synthases-1 and -2. Adv Immunol 1996;62:167–215
  • Jouzeau JY, Terlain B, Abid A, et al. Cyclo-oxygenase isoenzymes. How recent findings affect thinking about nonsteroidal anti-inflammatory drugs. Drugs 1997;53:563–82
  • Kalgutkar AS, Marnett AB, Crews BC, et al. Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors. J Med Chem 2000;43:2860–70
  • Herschman HR. Prostaglandin synthase 2. Biochim Biophys Acta 1996;1299:125–40
  • Dubois RN, Abramson SB, Crofford L, et al. Cyclooxygenase in biology and disease. FASEB J 1998;12:1063–73
  • Scheen AJ. Withdrawal of rofecoxib (Vioxx): what about cardiovascular safety of COX-2 selective non-steroidal anti-inflammatory drugs? Rev Med Liege 2004;59:565–9
  • Dogne JM, Supuran CT, Pratico D. Adverse cardiovascular effects of the coxibs. J Med Chem 2005;48:2251–7
  • Kaur J, Bhardwaj A, Huang Z, Knaus EE. N-1 and C-3 substituted indole Schiff bases as selective COX-2 inhibitors: synthesis and biological evaluation. Bioorg Med Chem Lett 2012;22:2154–9
  • Bandgar BP, Sarangdhar RJ, Viswakarma S, Ahamed FA. Synthesis and biological evaluation of orally active prodrugs of indomethacin. J Med Chem 2011;54:1191–201
  • Abdellatif KR, Chowdhury MA, Dong Y, et al. Dinitroglyceryl and diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of aspirin, indomethacin and ibuprofen: synthesis, biological evaluation and nitric oxide release studies. Bioorg Med Chem Lett 2009;19:3014–18
  • Huang Z, Velazquez CA, Abdellatif KR, et al. Ethanesulfohydroxamic acid ester prodrugs of nonsteroidal anti-inflammatory drugs (NSAIDs): synthesis, nitric oxide and nitroxyl release, cyclooxygenase inhibition, anti-inflammatory, and ulcerogenicity index studies. J Med Chem 2011;54:1356–64
  • Chowdhury MA, Huang Z, Abdellatif KR, et al. Synthesis and biological evaluation of indomethacin analogs possessing a N-difluoromethyl-1,2-dihydropyrid-2-one ring system: a search for novel cyclooxygenase and lipoxygenase inhibitors. Bioorg Med Chem Lett 2010;20:5776–80
  • Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996;384:644–8
  • Di Fiore A, Pedone C, D'Ambrosio K, et al. Carbonic anhydrase inhibitors: valdecoxib binds to a different active site region of the human isoform II as compared to the structurally related cyclooxygenase II “selective” inhibitor celecoxib. Bioorg Med Chem Lett 2006;16:437–42
  • Abdellatif KR, Chowdhury MA, Dong Y, et al. Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 5-(4-hydroxymethylphenyl)-1-(4-aminosulfonylphenyl)-3-trifluoromethyl-1H-pyrazole and its methanesulfonyl analog: synthesis, biological evaluation and nitric oxide release studies. Bioorg Med Chem 2008;16:9694–8
  • Pena-Lopez M, Neumann H, Beller M. Ruthenium-catalyzed synthesis of indoles from anilines and epoxides. Chemistry 2014;20:1818–24
  • Dou X, Yao W, Wen S, Lu Y. Facile regiospecific synthesis of 2,3-disubstituted indoles from isatins. Chem Commun (Camb) 2014;50:9469–72
  • El-Nezhawy AO, Biuomy AR, Hassan FS, et al. Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity. Bioorg Med Chem 2013;21:1661–70
  • Abdelazeem AH, Abdelatef SA, El-Saadi MT, et al. Novel pyrazolopyrimidine derivatives targeting COXs and iNOS enzymes; design, synthesis and biological evaluation as potential anti-inflammatory agents. Eur J Pharm Sci 2014;62:197–211

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.