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

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 31, Issue 2, 2016, Pages 318-324

  Abdellatif, Khaled R A ^a   Lamie, Phoebe F ^a   Omar, Hany A ^a,b  

^a Beni Suef University   (Egypt)

^b UNIVERSITY OF SHARJAH   (United Arab Emirates)

Author keywords

Anti inflammatory activity; Cyclooxygenase; Indomethacin; Molecular modeling

Indexed keywords

(3 METHYL 2 PHENYL INDOL 1 YL) PHENYL METHANONE; (4 CHLOROPHENYL) (3 METHYL 2 PHENYL INDOL 1 YL) METHANONE; (4 CHLOROPHENYL) (5 METHANESULFONYL 3 METHYL 2 PHENYL INDOL 1YL) METHANONE; (5 METHANESULFONYL 3 METHYL 2 PHENYL INDOL 1 YL) PHENYL METHANONE; 1 BENZYL 3 METHYL 2 PHENYL 1H INDOLE; 1 BENZYL 5 METHANESULFONYL 3 METHYL 2 PHENYL 1H INDOLE; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; CELECOXIB; FUNCTIONAL GROUP; INDOLE DERIVATIVE; INDOMETACIN; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE INHIBITOR;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; RAT; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; ENZYME ACTIVE SITE; IC50; METABOLISM; MOUSE; PRECLINICAL STUDY; PROCEDURES; STRUCTURE ACTIVITY RELATION; SYNTHESIS; WISTAR RAT;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CATALYTIC DOMAIN; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DRUG EVALUATION, PRECLINICAL; INDOLES; INDOMETHACIN; INHIBITORY CONCENTRATION 50; MICE; MOLECULAR DOCKING SIMULATION; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84955492460     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2015.1022174     Document Type: Article

References (22)

1. 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.
2. 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.
3. 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.
4. Smith WL, Dewitt DL. Prostaglandin endoperoxide H synthases-1 and-2. Adv Immunol 1996;62:167-215.
5. 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.
6. 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.
7. Herschman HR. Prostaglandin synthase 2. Biochim Biophys Acta 1996;1299:125-40.
8. Dubois RN, Abramson SB, Crofford L, et al. Cyclooxygenase in biology and disease. FASEB J 1998;12:1063-73.
9. 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.
10. Dogne JM, Supuran CT, Pratico D. Adverse cardiovascular effects of the coxibs. J Med Chem 2005;48:2251-7.
11. 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.
12. 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.
13. 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.
14. Huang Z, Velazquez CA, Abdellatif KR, et al. Ethanesulfohydroxamic acid ester prodrugs of nonsteroidal antiinflammatory drugs (NSAIDs): synthesis, nitric oxide and nitroxyl release, cyclooxygenase inhibition, anti-inflammatory, and ulcerogenicity index studies. J Med Chem 2011;54:1356-64.
15. 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.
16. 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.
17. 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.
18. 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.
19. Pena-Lopez M, Neumann H, Beller M. Ruthenium-catalyzed synthesis of indoles from anilines and epoxides. Chemistry 2014; 20:1818-24.
20. 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.
21. 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.
22. 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.