Aromatic amide derivatives of 5,6-dimethoxy-2,3-dihydro-1H-inden(-1-yl)acetic acid as anti-inflammatory agents free of ulcerogenic liability

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 24, 2007, Pages 6790-6796

  Sharma, Meenakshi ^a   Ray, S M ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Amides; Anti inflammatory; Indene; Ulcerogenicity

Indexed keywords

5,6 DIMETHOXY 2,3 DIHYDRO 1H INDEN 1 YLACETIC ACID DERIVATIVE; ACETIC ACID; ACETYLSALICYLIC ACID; AMIDE; ANTIINFLAMMATORY AGENT; INDOMETACIN; LIPOPOLYSACCHARIDE; PROADIFEN; UNCLASSIFIED DRUG;

ADJUVANT ARTHRITIS; ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTIPYRETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; EDEMA; FEVER; GASTROINTESTINAL TOXICITY; INFLAMMATION; MALE; MOUSE; NONHUMAN; PAIN; WRITHING TEST;

ACETIC ACIDS; AMIDES; ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS; ARTHRITIS; CARRAGEENAN; CYTOCHROME P-450 ENZYME SYSTEM; EDEMA; ENZYME INHIBITORS; INDENES; MALE; MICE; MOLECULAR STRUCTURE; RATS; ULCER;

EID: 35848952056     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.10.037     Document Type: Article

References (35)

1. Ganellin C.R. In: Harper N.J., and Simmonds A.B. (Eds). Advances in Drug Research Vol. 4 (1967), Academic Press, London 163-249
2. Woltersclorf Jr. O.W., Desolms S.J., and Cragoe Jr. E.J. J. Med. Chem. 24 (1981) 874
3. Lahiri S.C., and De N.C. J. Med. Chem. 11 (1968) 900
4. Ray S.M., and Lahiri S.C. J. Indian Chem. Soc. 68 (1991) 549
5. Karaguni I.M., Glusenkamp K.H., Langerak A., Geisen C., Ullrich V., Winde G., Moroy T., and Muller O. Bioorg. Med. Chem. Lett. 12 (2002) 709
6. Chairini A., Ferranti A., Giovanninetti G., and Matteuzzi D. Farmaco[Sci.] 35 (1980) 413
7. Sheng R., Lin X., Li J., Jiang Y., Shang Z., and Hu Y. Bioorg. Med. Chem. Lett. 15 (2005) 3834
8. Molteni V., Rhodes D., Rubins K., Hansen M., Bushman F.D., and Siegel J.S. J. Med. Chem. 43 (2000) 2031
9. Hall I.H., Wong O.T., Chi L.K., and Chen S.Y. Anticancer Res. 14 (1994) 2053
10. Mignani S., Bohme G.A., Birraux G., Boireau A., Jimonet P., Damour D., Genevois-Borella A., Debono M.-W., Pratt J., Vuilhorgne M., et al. Bioorg. Med. Chem. 10 (2002) 1627
11. Musso D.L., Cochran F.R., Kelley J.L., McLean E.W., Selph J.L., Rigdon G.C., Orr G.F., Davis R.G., Cooper B.R., Styles V.L., Thompson J.B., and Hall W.R. J. Med. Chem. 46 (2003) 399
12. Sterling J., Herzig Y., Goren T., Finkelstein N., Lerner D., Goldenberg W., Miskolczi I., Molnar S., Rantal F., Tamas T., Toth G., Zagyva A., Zekany A., Lavian G., Gross A., Friedman R., Razin M., Huang W., Krais B., Chorev M., Youdim M.B., and Weinstock M. J. Med. Chem. 45 (2002) 5260
13. Juby P.F., Goodwin W.R., Hudyma T.W., and Partyka R.A. J. Med. Chem. 15 (1972) 1297
14. Ray S.M., and Lahiri S.C. J. Ind. Chem. Soc. 67 (1990) 324
15. Aono T., Kishimoto S., Araki Y., and Noguchi S. Chem. Pharm. Bull. 25 (1977) 3198
16. Noguchi S., Kishimoto S., Minamida I., Obayashi M., and Kawakita K. Chem. Pharm. Bull. 19 (1971) 646
17. Wiesenberg-Boettcher I., Schweizer A., and Muller K. Agents Actions 26 (1989) 240
18. Kalgutkar A.S., Crews B.C., Rowlinson S.W., Marnett A.B., Kozak K.R., Remmel R.P., and Marnett L.J. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 925
19. Kalgutkar A.S., Marnet A.B., Crews C.B., Remmel R.P., and Marnett L.S. J. Med. Chem. 43 (2000) 2860
20. Kalgutkar A.S., Rowlinson S.W., Crews B.C., and Marnett L.J. Bioorg. Med. Chem. Lett. 12 (2002) 521
21. Zovko M., Zorc B., Takac M.J., Metelko B., and Novak P. CCACAA 76 (2003) 335
22. Vogel's Textbook of Practical Organic Chemistry, Furniss, B.S.; Hannaford, A.J.; Smith, P.W.G.; Tatchell, A.R. Eds; Pearson Education; 2004; p 987.
23. Lahiri S.C., and Gupta J.K. J. Indian Chem. Soc. LIII (1976) 1040
24. Balsamo A., Barili P.L., Crotti P., Macchia F., Pecchia A., Cuttica A., and Passerini N. J. Med. Chem. 18 (1975) 842
25. 2, 4H), 4.18 (t, CH, 1H), 6.64 (s, ArH, H), 6.73 (s, ArH, 2H).
26. 3, 3H), 6.81 (m, ArH, 3H), 10.08 (br s, COOH, 2H).
27. 3, 3H), 7.00 (s, ArH, 1H), 7.15 (s, ArH, 1H), 10.12 (br s, COOH, 1H).
28. +).
29. 3, brine, and water. The organic phase was dried with anhydrous sodium sulfate and then distilled off to obtain the amides.
30. Winter C.A., Risely E.A., and Nuss G.M. Proc. Soc. Exp. Biol. Med. 111 (1962) 544
31. Somchit N., Wong C.W., Zuraini A., Bustamam A.A., Hasiah A.H., Khairi H.M., Sulaiman M.R., and Israf D.A. Drug Chem. Toxicol. 29 (2006) 237
32. Collier H.O., Dinneen L.C., Johnson C.A., and Schneider C. Br. J. Pharmacol. 32 (1968) 295
33. Dogan D.M., Ataoglu H., and Akarsu E.S. Fundam. Clin. Pharmacol. 16 (2002) 303
34. Newbould B.B. Br. J. Pharmac. Chemother. 21 (1963) 127
35. Vela'zquez C., Rao P.N.P., and Knaus E.E. J. Med. Chem. 48 (2005) 4061