Synthesis and antiinflammatory activity of coumarin derivatives

Journal of Medicinal Chemistry

Volumn 48, Issue 20, 2005, Pages 6400-6408

  Kontogiorgis, Christos A ^a   Hadjipavlou Litina, Dimitra J ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 7 HYDROXY 8 PIPERAZINE 1 YLMETHYL CHROMEN 2 ONE; ANTIINFLAMMATORY AGENT; ARACHIDONIC ACID; BUTYLCRESOL; CARRAGEENAN; COUMARIN DERIVATIVE; CYCLOOXYGENASE 1; FREUND ADJUVANT; HEMOPROTEIN; HYDROXYL RADICAL; INDOMETACIN; NORDIHYDROGUAIARETIC ACID; SUPEROXIDE; TROLOX C; UNCLASSIFIED DRUG; WARFARIN; ZOXAZOLAMINE;

ADJUVANT ARTHRITIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONFERENCE PAPER; CONTROLLED STUDY; DISEASE SEVERITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; EDEMA; ENZYME INHIBITION; FEMALE; INFLAMMATION; INFRARED SPECTROSCOPY; LIPID PEROXIDATION; LIPOPHILICITY; MALE; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SCORING SYSTEM; TREATMENT OUTCOME; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARTHRITIS, EXPERIMENTAL; CARRAGEENAN; COUMARINS; CYCLOOXYGENASE INHIBITORS; EDEMA; FEMALE; FREE RADICAL SCAVENGERS; IMMUNOLOGIC FACTORS; LIPOXYGENASE INHIBITORS; MALE; MANNICH BASES; RATS; RATS, INBRED F344; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES;

EID: 26444461246     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0580149     Document Type: Conference Paper

References (46)

1. Killer, P. L.; Hodd, K. O.; Wilson, R. L. Antiinflammatory drugs: Protection of a Bacteria virus as an in vitro biological measure of free radical activity. Chem.-Biol. Interact. 1983, 47, 293-305.
2. Egan, D.; O'Kennedy, E.; Moran, E.; Cox, D.; Prosser, E.; Thornes, R. D. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds. Drug. Metab. Rev. 1990, 22, 503-529.
3. Murray, R. D. H.; Mendez, I.; Brawn, S. A. The Natural Coumarins; Wiley: New York, 1982.
4. Piller, N. B. A comparison of the effectiveness of some antiinflammatory drugs on thermal oedema. Br. J. Exp. Pathol. 1975, 56, 554-559.
5. Piller, N. B.; Casley-Smith, J. R. The effect of coumarin on protein and PVP clearance from rat legs with various high protein oedemas. Br. J. Exp. Pathol. 1975, 56, 439-445.
6. Fylaktakidou, K.; Hadjipavlou-Litina, D.; Litinas, K.; Nicolaides, D. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activity. Cur. Pharm. Des. 2004, 30, 3813-3833.
7. Neichi, T.; Koshihara, Y.; Mutora, S. I. Inhibitory effect of esculetin on 5-lipoxygenase and leukotriene biosynthesis. Biochim. Biophys. Acta 1983, 753, 130-2.
8. 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, 224-9.
9. Craven, P. A.; Pfanstiel, J.; De Rubertis F. R. Role of reactive oxygen in bile salt stimulation of colonic epithelial proliferation. J. Clin. Invest. 1986, 77, 850-9.
10. Ozaki, Y.; Ohashi, T.; Niwa, Y. A comparative study on the effects of inhibitors of the lipoxygenase pathway on neutrophil function. Inhibitory effects on neutrophil function may not be attributed to inhibition of the lipoxygenase pathway. Biochem. Pharmacol. 1986, 35, 3481-8.
11. Paya, M.; Halliwell, B.; Hoult, J. R. S. Interactions of a series of coumarins with reactive oxygen species. Scavenging of superoxide, hypochlorous acid and hydroxyl radicals. Biochem. Pharmacol. 1992, 44, 205-14.
12. Mora, A.; Paya, M.; Rios, J. L.; Alcaraz, M. J. Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of nonenzymic lipid peroxidation. Biochem. Pharmacol. 1990, 40, 793-7.
13. Desai, R. B. Mannich Reaction with Hydroxycoumarins. J. Org. Chem. 1961, 26, 5251-5253.
14. Da Re, P.; Bonola, G.; Verlicchi, L. A series of Coumarin Derivatives with Central Stimulating Activity. J. Med. Chem. 1964, 7, 162-166.
15. Patel, M. G.; Sethna, S. Application of the Mannich reaction to some coumarin derivatives. J. Indian Chem. Soc. 1962, 39, 595-598.
16. Hadjipavlou-Litina, D.; Geronikaki, A.; Sotiropoulou, E. Antiinflammatory activity of aminoketone derivatives of 2,4-disubstituted thiazoles Res. Commun. Chem. Pathol. Pharm. 1993, 790, 355-362.
17. Gavalas, A.; Hadjipetrou, L.; Kourounakis, P. Synthesis of novel derivatives of Aroylamino alcohols and 3-amino-substituted-1-phenylpropanols with potential anti-inflammatory and immunomodulating activities J. Pharm. Pharmacol. 1998, 50, 583-591.
18. Satyanarayana, D.; Gorge, S.; Subrahmanyam, E. V.; Kalluraya, B. Studies on the synthesis and biological activity of 3-arylaminomethyl-5-(3-pyridyl)-1,3, 4-oxadiazole-2-thione derivatives. Boll. Chim. Farm. 2001, 140, 228-32.
19. Day, R. O.; Graham, G. G.; Williams, K. M.; Brooks, P. M. Variability in response to NSAIDs. Fact or fiction? Drugs 1988, 643-651.
20. Ellis, G. A.; Blake D. R. Why are nonsteroidal anti-inflammatory drugs so variable in their efficacy? A description of ion trapping. Ann. Rheum. Dis. 1993, 241-243.
21. Brooks, P. M.; Day, R. O. Non steroidal anti-inflammatory drugs - differences and similarities. N. Eng. J. Med. 1988, 1716-1725.
22. Shanbag, V. R.; Crider, M. A.; Gohkale; R.; Harpalani, A.; Dick, R. M. Ester amide and prodrugs of ibuprofen and naproxen. Synthesis, anti-inflammatory activity and gastrointestinal toxicity. J. Pharm. Sci. 1992, 149-154.
23. Molho, D.; Boschetti, E. 7-Hydroxy-8-(dialkylaminomethyl)-coumarins. Fr 1,310,535, 1962, p 7.
24. Gupta, V. N.; Sharima, B. R.; Avora, R. B. Pharmacologically active coumarin derivatives. I. Mannich bases from umbelliferone and 4-methylumbelliferone. J. Sci. Indust. Res. 1961, 20B, 300.
25. Kontogiorgis, C.; Hadjipavlou-Litina, D. Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidants agents. J. Enzymol. Inhib. Med. Chem. 2003, 18, 63-69.
26. Hansch, C.; Leo, A. J. In Exploring QSAR Fundamentals and applications in Chemistry and Biology, ACS Professional Reference Book, Washington, D. C.; Heller, S. R., consulting ed.; 1995, Chapter 7, Vol. I, pp 279-280.
27. Biobyte Corp., C.-QSAR Database 201 West 4th St., Suite 204, Claremont, CA 91711.
28. Shen, T. Y. Non steroidal antiinflammatory agents. In Burger's Medicinal Chemistry; Wolf, M. E., Ed.; John Wiley and Sons: New York, 1980; pp 1217-1219.
29. Winter, C. A. In Nonsteroidal Antiinflammatory Drugs; Gattini, S., Dukes, M. N. G., Eds.; Excepta Medica: Amsterdam, 1965; p 190.
30. Kuroda, T.; Suzuki, F.; Tamura, T.; Ohmori, K.; Hosoe, H. A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl- 1,8-naphthyridine-3-carboxamides. J. Med. Chem. 1992, 1130-1136.
31. Tegtmeier, M.; Legrum, W. 7-Amino-coumarins as substrates of cytochrome P450-isozymes. Arch. Pharm. (Weinheim, Ger.) 1998, 331, 143-148.
32. Taraborewala, R. B.; Kauffman, J. M. Antiinflammatory activity of quinazolinoformazans. J. Pharm. Sci. 1990, 173-178.
33. Muller, K. 5-Lipoxygenase and 12-Lipoxygenase: Attractive targets for the development of novel antipsoriatic Drugs, Reviews and Trends. Arch. Pharm. 1994, 327, 3-19.
34. Kemal, C.; Louis-Flamberg, P.; Krupinski-Olsen, R.; Shorter, A. L. Reductive inactivation of soybean lipoxygenase I by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry 1987, 26, 7064-7072.
35. Van der Zee, J.; Elimg, T. E.; Mason, R. P. Formation of free radical metabolites in the reaction between soybean lipoxygenase and its inhibitors. An ESR study. Biochemistry 1988, 32, 171-181.
36. (a) Hadjipavlou-Litina, D.; Pontiki, E. Quantitative Structure Activity Relationships on Lipoxygenase Inhibitors. Internet Electron. J. Mol. Des. 2002, 1, 134-141.
37. (b) Pontiki, E.; Hadjipavlou-Litina D. (Review) Quantitative Structure Activity Relationships on Lipoxygenase Inhibitors. Mini Rev. Med. Chem. 2003, 3, 487-499.
38. Flohe, L.; Beckman, R.; Giertz, H.; Loschen, G. Oxygen-centered free radicals as mediators of inflammation. In Oxidative Stress; Sies H. Ed.; Academic Press: London, 1985, pp 403-435.
39. Saldan, L. A.; Elias, G.; Gao, M. N. A. Oxygen radical scavenging activity of phenylbutenones and their correlation with anti-inflammatory activity. Arzneim-forsch./Drug Res. 1990, 40, 89-91.
40. Verloop A. The sterimol approach to drug design; Marcell Dekker: New York, 1987.
41. Aruoma, O. I.; Wasil, M.; Halliwell, B.; Hoey, B.; Butler, J. The scavenging of oxidants by sulphasalazine and its metabolites. A possible contribution to their anti-inflammatory effects? Biochem. Pharmacol. 1987, 36, 3739-3742.
42. Burke W. J.; Kolbenzen, M. J.; Stephens, C. W. Condensation of naphthols with Formaldehyde and Primaru amines J. Am. Chem. Soc. 1952, 74, 3601-3605.
43. Kulmacz, R. J.; Lands, W. E. M. Cyclooxygenase: measurement, purification and properties. In Prostaglandins and related substances: apratical approach; Benedetto C., McDonald-Gibson R. G., Nigam S., Slater T. F., Eds., Irl. Press: Oxford (England), 1987; p 209.
44. Jeding, I.; Evans J. P.; Akanmu, D.; Dexter, D.; Spencer, D. J.; Aruoma, I. O.; Jenner, P.; Halliwell, B. Characterization of the potential antioxidant and pro-oxidant actions of some neuroleptic drugs. Biochem. Pharmacol. 1995, 49, 359-366.
45. Evans, J. P.; Cecchini, R.; Halliwell, B. Oxidative damage to lipids and alpha-1 antiproteinase by phenylbutazone in the presence of haem proteins: protection by ascorbic acid. Biochem. Pharmacol. 1992, 44, 981-984.
46. Candan, F. Effect of Rhus coribum L. (Aracardiaceae) on superoxide radical scavenging anf xanthine oxidase activity. J. Enzymol. Inhib. Med. Chem. 2003, 18, 59-62.