Synthesis of 2-methyl-3-indolylacetic derivatives as anti-inflammatory agents that inhibit preferentially cyclooxygenase 1 without gastric damage

Journal of Medicinal Chemistry

Volumn 49, Issue 26, 2006, Pages 7774-7780

  Perissutti, Elisa ^a   Fiorino, Ferdinando ^a   Renner, Christian ^b   Severino, Beatrice ^a   Roviezzo, Fiorentina ^a   Sautebin, Lidia ^a   Rossi, Antonietta ^a   Cirino, Giuseppe ^a   Santagada, Vincenzo ^a   Caliendo, Giuseppe ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 3 INDOLYLACETIC ACID DERIVATIVE; [5 METHOXY 2 METHYL 1 (1 METHYLPIPERIDIN 4 YL) 1H INDOL 3 YL]ACETIC ACID; [5 METHOXY 2 METHYL 1 (1 METHYLPIPERIDIN 4 YL) 1H INDOL 3 YL]ACETIC ACID ETHYL ESTER; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; DRUG TOLERABILITY; ENZYME INHIBITION; GASTROINTESTINAL TRACT; IN VITRO STUDY; IN VIVO STUDY; MALE; MOLECULAR MODEL; MOUSE; NONHUMAN; RAT; SIMULATION;

ACUTE DISEASE; ANIMALS; ANTI-INFLAMMATORY AGENTS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DRUG EVALUATION, PRECLINICAL; EDEMA; INDOLEACETIC ACIDS; MEMBRANE PROTEINS; MODELS, MOLECULAR; RATS; STOMACH; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33845916256     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0608199     Document Type: Article

References (18)

1. Roller, A.; Bahr, O. R.; Streffer, J.; Winter, S.; Heneka, M.; Deininger, M.; Meyermann, R.; Naumann, U.; Gulbins, E.; Weller, M. Selective potentiation of drug cytotoxicity by NSAID in human glioma cells: the role of COX-1 and MRP. Biochem. Biophys. Res. Commun. 1999, 259, 600-605.
2. Lu, J. X.; Shen, Qi.; Jiang, J. H.; Shen, G. L.; Yu. R. Q. QSAR analysis of cyclooxygenase inhibitor using particle swarm optimization and multiple linear regression. J. Pharm. Biomed. Anal. 2004, 35, 679-687.
3. Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2005, 15, 1793-1797.
4. Chen, Q. H.; Rao, P. N. P.; Knaus, E. E. Design, synthesis, and biological evaluation of N-acetyl-2-carboxybenzenesulfonamides: a novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. 2005, 13, 2459-2468.
5. Rao, P. N. P.; Uddin, Md. J.; Knaus, E. E. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004, 47, 3972-3990.
6. Grosser, T.; Fries, S.; FitzGerald, A. G. Biological basis for the cardiovascular consequences of COX 2 inhibition: therapeutic challenges and opportunities. J. Clin. Invest. 2006, 116, 4-15.
7. Cullen, L.; Kelly, L.; Connor, S. O.; Fitzgerald, D. J. Selective cyclooxygenase-2 inhibition by nimesulide in man. J. Pharmacol. Exp. Ther. 1998, 287 (2), 578-582.
8. Futaki, N.; Takahashi, S.; Kitagawa, T.; Yamakawa, Y.; Tanaka, M.; Higuchi, S. Selective inhibition of cyclooxygenase-2 by NS-398 in endotoxin shock rats in vivo. Inflammation Res. 1997, 46 (12), 496-502.
9. Kirchner, T.; Argentieri, D. C.; Barbone, A. G.; Singer, M.; Steber, M.; Ansell, J.; Beers, S. A.; Wachter, M. P.; Wu, W.; Malloy, E.; Stewart, A.; Ritchie, D. M. Evaluation of the anti-inflammatory activity of a dual cyclooxygenase 2 selective/5-lipoxygenase inhibitor, RWJ 63556, in a canine model of inflammation. J. Pharmacol. Exp. Ther. 1997, 282 (2), 1094-1101.
10. Borch, R. F.; Berstein, M. D.; Durst, H. D. Cyanohydridoborate, anion as a selective reducing agent. J. Am. Chem. Soc. 1971, 93, 2897-2904.
11. Westheimer, F. H.; Taguchi, K. Catalysis by molecular sieves in the preparation of ketimines and enamines. J. Org. Chem. 1971, 36, 1570-1572.
12. Wallace, J. L.; Mcnight, W.; Reuter, B. K. NSAID-induced gastric damage in rats: requirement for inhibition of both cyclooxygenase 1 and 2. Gastroenterology 2000, 119 (3), 706-714.
13. Brenneis, C.; Maier, T. J.; Schmidt, R.; Hofacker, A.; Zulauf, L.; Jakobsson, P. J.; Scholich, K.; Geisslinger, G. Inhibition of prostaglandin E2 synthesis by SC-560 is independent of cyclooxygenase 1 inhibition. FASEB J. 2006, 20, 1352-1360.
14. Martinez, R. V.; Reval, M.; Campos, M. D.; Terron, J. A.; Dominguez, R.; Lopez-Munoz, F. J. Involvement of peripheral cyclooxygenase-1 and cyclooxygenase-2 in inflammatory pain. J. Pharm. Pharmacol. 2002, 54, 405-412.
15. Kurumbail, R. G.; Stevens, A. M.; Gierse, J. K.; Mcdonald, J. J.; Stegeman, R. A.; Pak, J. Y.; Gildehaus, D.; Miyashiro, J. M.; Penning, T. D.; Seibert, K.; Isakson, P. C.; Stallings, W. C. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996, 384, 644-648.
16. Zingarelli, B.; Southan, G. J.; Gilad, E.; O'Connor, M.; Salzman, A. L.; Szabò, C. The inhibitory effects of mercaptoalkylguanidines on cyclooxygenase activity. Br. J. Pharmacol. 1997, 120, 357-366.
17. Sautebin, L.; Lanaro, A.; Rombolà, L.; Ialenti, A.; Sala, A.; Di Rosa, M. Cyclooxygenase-2-dependent generation of 8-epiprostaglandin p2a by lipopolysaccharide-activated J774 macrophages. Inflammation Res. 1999, 48, 503-508.
18. Davies, N. M.; Roseth, A. G.; Aplleyard, C. B.; McKnight, W.; Del Soldato, P.; Calignano, A.; Cirino, G.; Wallace, J. L. NO-naproxen vs. naproxen: ulcerogenic, analgesic and anti-inflammatory effects. Aliment. Pharmacol. Ther. 1997, 11, 69-79.