Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 26, Issue 6, 2011, Pages 767-776

  Akhter, Mymoona ^a   Akhter, Nayeema ^b   Alam, M M ^a   Zaman, M S ^a   Saha, Rikta ^a   Kumar, A ^c  

^a HAMDARD UNIVERSITY   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

^c TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

Anti inflammatory agents; Cyclooxygenase; Lipoxygenase; Oxadiazole

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 3 (5 O TOLYLAMINO [1,3,4]OXADIAZOL 2 YL) CHROMEN 2 ONE; 3 (5 P TOLYL [1,3,4]OXADIAZOL 2 YL) CHROMEN 2 ONE; 3 (5 P TOLYLAMINO [1,3,4]OXADIAZOL 2 YL) CHROMEN 2 ONE; 3 (5 PHENYL [1,3,4]OXADIAZOL 2 YL) CHROMEN 2 ONE; 3 (5 PHENYLAMINO [1,3,4]OXADIAZOL 2 YL) CHROMEN 2 ONE; 3 [5 (2,4 DICHLORO PHENYL) [1,3,4]OXADIAZOL 2 YL] CHROMEN 2 ONE; 3 [5 (3 CHLORO PHENYLAMINO) [1,3,4]OXADIAZOL 2 YL] CHROMEN 2 ONE; 3 [5 (4 CHLORO PHENYL) [1,3,4]OXADIAZOL 2 YL] CHROMEN 2 ONE; 3 [5 (4 CHLORO PHENYLAMINO) [1,3,4]OXADIAZOL 2 YL] CHROMEN 2 ONE; 3 [5 (4 METHOXY PHENYLAMINO) [1,3,4]OXADIAZOL 2 YL] CHROMEN 2 ONE; 3 [5 (4 METHOXYPHENYL) [1,3,4]OXADIAZOL 2 YL] CHROMEN 2 ONE; 4 METHOXY N [5 (2 OXO 2H CHROMEN 3 YL) [1,3,4]OXADIAZOL 2 YL] BENZAMIDE; 4 METHYL N [5 (2 OXO 2H CHROMEN 3 YL) [1,3,4]OXADIAZOL 2 YL] BENZAMIDE; ARACHIDONATE 12 LIPOXYGENASE; ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DICLOFENAC; IBUPROFEN; INDOMETACIN; N [5 (2 OXO 2H CHROMEN 3 YL) [1,3,4]OXADIAZOL 2 YL] BENZAMIDE; N [5 (2 OXO 2H CHROMEN 3 YL) [1,3,4]OXADIAZOL 2 YL] BENZAMIDE DERIVATIVE; NAPROXEN; ROFECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; LIPID PEROXIDATION; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL; RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CARRAGEENAN; EDEMA; ENZYME INHIBITORS; LIPID PEROXIDATION; LIPOXYGENASES; OXADIAZOLES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RATS; RATS, WISTAR; STOMACH ULCER; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 81355161057     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2010.550890     Document Type: Article

References (51)

1. Fiorucci S, Meli R, Bucci M, Cirino G. Dual inhibitors of cyclooxygenase and 5-lipoxygenase. A new avenue in anti-inflammatory therapy? Biochem Pharmacol 2001;62:1433-1438. (Pubitemid 33145286)
2. Smith WL, Marnett LJ. Prostaglandin endoperoxide synthase: structure and catalysis. Biochim Biophys Acta 1991;1083:1-17.
3. Dannhardt G, Kiefer W. Cyclooxygenase inhibitors-current status and future prospects. Eur J Med Chem 2001;36:109-126. (Pubitemid 32304514)
4. Fosslien E. Adverse effects of nonsteroidal anti-inflammatory drugs on the gastrointestinal system. Ann Clin Lab Sci 1998;28:67-81. (Pubitemid 28164809)
5. Goldenberg MM. Celecoxib, a selective cyclooxygenase-2 inhibitor for the treatment of rheumatoid arthritis and osteoarthritis. Clin Ther 1999;21:1497-1513; discussion 1427. (Pubitemid 29449551)
6. Vane JR, Bakhle YS, Botting RM. Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol 1998;38:97-120. (Pubitemid 28231490)
7. Mukherjee D. Selective cyclooxygenase-2 (COX-2) inhibitors and potential risk of cardiovascular events. Biochem Pharmacol 2002;63:817-821. (Pubitemid 34242993)
8. Parente L, Perretti M. Advances in the pathophysiology of constitutive and inducible cyclooxygenases: two enzymes in the spotlight. Biochem Pharmacol 2003;65:153-159. (Pubitemid 36015818)
9. Samuelsson B, Borgeat P, Hammaratrom S, Murphy RC. Leukotrienes: a new group of biologically active compounds. Adv Prostaglandin Thromboxane Res 1980;6:1-18.
10. Samuelsson B. Leukotrienes and other lipoxygenase products. Prog Lipid Res 1986;25:13-18.
11. Charlier C, Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem 2003;38:645-659. (Pubitemid 36980661)
12. McMillan RM, Walker ERH. Designing therapeutically effective 5-lipoxygenase inhibitors. Trends Pharmacol Sci 1992;13:323-327.
13. Ford-Hutchinson AW, Gresser M, Young RN. 5-Lipoxygenase. Annu Rev Biochem 1994;63:383-386.
14. Young RN. Inhibitors of 5-lipoxygenase: a therapeutic potential yet to be fully realized? Eur J Med Chem 1999;34:671-685. (Pubitemid 29491553)
15. Vila L. Cyclooxygenase and 5-lipoxygenase pathways in the vessel wall: role in atherosclerosis. Med Res Rev 2004;24:399-424. (Pubitemid 38802696)
16. Zhao L, Funk CD. Lipoxygenase pathways in atherogenesis. Trends Cardiovasc Med 2004;14:191-195. (Pubitemid 38942827)
17. Kayama Y, Minamino T, Toko H, Sakamoto M, Shimizu I, Takahashi H et al. Cardiac 12/15 lipoxygenase-induced inflammation is involved in heart failure. J Exp Med 2009;206:1565-1574.
18. Rotondo S, Dell'Elba G, Krauze-Brzósko K, Manarini S, Martelli N, Pecce R et al. Licofelone, a dual lipoxygenase-cyclooxygenase inhibitor, downregulates polymorphonuclear leukocyte and platelet function. Eur J Pharmacol 2002;453:131-139. (Pubitemid 35232463)
19. Pommery N, Taverne T, Telliez A, Goossens L, Charlier C, Pommery J et al. New COX-2/5-LOX inhibitors: apoptosis-inducing agents potentially useful in prostate cancer chemotherapy. J Med Chem 2004;47:6195-6206. (Pubitemid 39587244)
20. Vijayakrishnan R, Rao GS. A computer modeling approach towards designing dual LOX/COX inhibitors as potent anti-cancer drugs. Biophys J 2009;94:1090.
21. Holla BS, Gonsalves R, Shenoy S. Synthesis and antibacterial studies of a new series of 1,2-bis(1,3, 4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2, 4-triazol-3-yl)ethanes. Eur J Med Chem 2000;35:267-271. (Pubitemid 30165690)
22. Macaev F, Rusu G, Pogrebnoi S, Gudima A, Stingaci E, Vlad L et al. Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure-anti-mycobacterial activities. Bioorg Med Chem 2005;13:4842-4850. (Pubitemid 40943508)
23. Liu F, Luo XQ, Song BA, Bhadury PS, Yang S, Jin LH et al. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4- oxadiazole moiety. Bioorg Med Chem 2008;16:3632-3640. (Pubitemid 351484045)
24. Burbuliene MM, Jakubkiene V, Mekuskiene G, Udrenaite E, Smicius R, Vainilavicius P. Synthesis and anti-inflammatory activity of derivatives of 5-[(2-disubstituted amino-6-methyl-pyrimidin- 4-yl)-sulfanylmethyl]-3H-1,3,4- oxadiazole-2-thiones. Farmaco 2004;59:767-774. (Pubitemid 39335947)
25. Palaska E, Sahin G, Kelicen P, Durlu NT, Altinok G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4- oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Farmaco 2002;57:101-107. (Pubitemid 34175107)
26. Amir M, Shikha K. Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6- dichloroanilino) phenyl]acetic acid derivatives. Eur J Med Chem 2004;39:535-545. (Pubitemid 38746763)
27. Zarghi A, Tabatabai SA, Faizi M, Ahadian A, Navabi P, Zanganeh V et al. Synthesis and anticonvulsant activity of new 2-substituted- 5-(2- benzyloxyphenyl)-1,3,4-oxadiazoles. Bioorg Med Chem Lett 2005;15:1863-1865. (Pubitemid 40380748)
28. Liu KG, Smith JS, Ayscue AH, Henke BR, Lambert MH, Leesnitzer LM et al. Identification of a series of oxadiazole-substituted alpha-isopropoxy phenylpropanoic acids with activity on PPARalpha, PPARgamma, and PPARdelta. Bioorg Med Chem Lett 2001;11:2385-2388. (Pubitemid 32781705)
29. Kumar D, Sundaree S, Johnson EO, Shah K. An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents. Bioorg Med Chem Lett 2009;19:4492-4494.
30. Emam AA, Deeb OA, Al-Omar M, Lehmann J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)- 2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3- substituted aminomethyl-1,3,4- oxadiazoline-2-thiones. J Bioorg Med Chem 2004;12:5107-5113.
31. Khan MT, Choudhary MI, Khan KM, Rani M, Atta-ur-Rahman.Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. Bioorg Med Chem 2005;13:3385-3395. (Pubitemid 40545793)
32. Farooqui M, Bora R, Patil CR. Synthesis, analgesic and anti-inflammatory activities of novel 3-(4-acetamido-benzyl)-5- substituted-1,2,4-oxadiazoles. Eur J Med Chem 2009;44:794-799.
33. Srivastava RM, de Almeida Lima A, Viana OS, da Costa Silva MJ, Catanho MT, de Morais JO. Antiinflammatory property of 3-aryl-5- (n-propyl)-1,2,4- oxadiazoles and antimicrobial property of 3-aryl- 5-(n-propyl)-4,5-dihydro-1,2, 4-oxadiazoles: their syntheses and spectroscopic studies. Bioorg Med Chem 2003;11:1821-1827. (Pubitemid 36349163)
34. Velázquez C, Rao PN, McDonald R, Knaus EE. Synthesis and biological evaluation of 3,4-diphenyl-1,2,5-oxadiazole-2- oxides and 3,4-diphenyl-1,2,5-oxadiazoles as potential hybrid COX-2 inhibitor/nitric oxide donor agents. Bioorg Med Chem 2005;13:2749-2757. (Pubitemid 40387485)
35. Grimm EL, Brideau C, Chauret N, Chan CC, Delorme D, Ducharme Y et al. Substituted coumarins as potent 5-lipoxygenase inhibitors. Bioorg Med Chem Lett 2006;16:2528-2531.
36. Alka K, Vasant KA, Rao MNA. Anti-inflammatory activity of cinnamic acids. Pharmazie 1989;44:870-873.
37. Maddi V, Raghu KS, Rao MN. Synthesis and anti- nflammatory activity of 3-(benzylideneamino)coumarins in rodents. J harm Sci 1992;81:964-966.
38. Kimura Y, Okuda H, Arichi S, Baba K, Kozawa M. Inhibition of the formation of 5-hydroxy-6,8,11,14-eicosatetraenoic acid from arachidonic acid in polymorphonuclear leukocytes by various coumarins. Biochim Biophys Acta 1985;834:224-229.
39. Celotti F, Laufer S. Anti-inflammatory drugs: new multitarget compounds to face an old problem. The dual inhibition concept. Pharmacol Res 2001;43:429-436. (Pubitemid 32578858)
40. Akhter M, Husain A, Azad B, Ajmal M. Aroylpropionic acid based 2,5-disubstituted-1,3,4-oxadiazoles: synthesis and their anti-inflammatory and analgesic activities. Eur J Med Chem 2009;44:2372-2378.
41. Khan MSY, Akhter M. Synthesis of some new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their biological activity. Indian J Chem 2003;42B:900-904.
42. Horning EC, Horning MG, Dimming DA. Organic Synthesis, Collective Vol. 3. New York: John Wiley & Sons Inc.; 1995, pp. 165-167.
43. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. Miscellaneous aromatic nitrogen compound. Vogel's Textbook of Practical Organic Chemistry. ngland: Addison Wesley Longman Limited; 1998, pp. 966.
44. Yar MS, Siddiqui AA, Ali MA. Synthesis and anti tuberculostatic activity of novel 1,3,4-oxadiazole derivatives. J Chin Chem Soc 2007;54:5-8.
45. Winter CA, Risley EA, Nuss GW. Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs. Proc Soc Exp Biol Med 1962;111:544-547.
46. Fukawa K, Kawano O, Hibi M, Misaki N, Ohba S, Hatanaka Y. A method for evaluating analgesic agents in rats. J Pharmacol Methods 1980;4:251-259. (Pubitemid 11232113)
47. Cioli V, Putzolu S, Rossi V, Scorza Barcellona P, Corradino C. The role of direct tissue contact in the production of gastrointestinal ulcers by anti-inflammatory drugs in rats. Toxicol Appl Pharmacol 1979;50:283-289. (Pubitemid 10233388)
48. Ohkawa H, Ohishi N, Yagi K. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 1979;95:351-358. (Pubitemid 9194347)
49. Carter GW, Young PR, Albert DH, Bouska J, Dyer R, Bell RL et al. 5-Lipoxygenase inhibitory activity of zileuton. J Pharmacol Exp Ther 1991;256:929-937.
50. Romano M, Chen XS, Takahashi Y, Yamamoto S, Funk CD, Serhan CN. Lipoxin synthase activity of human platelet 12-lipoxygenase. Biochem J 1993;296 (Pt 1):127-133. (Pubitemid 23344739)
51. Auerbach BJ, Kiely JS, Cornicelli JA. A spectrophotometric microtiter-based assay for the detection of hydroperoxy derivatives of linoleic acid. Anal Biochem 1992;201:375-380.