Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 23, 2007, Pages 6439-6443

  Burguete, Asunción ^a   Pontiki, Eleni ^b   Hadjipavlou Litina, Dimitra ^b   Villar, Raquel ^a   Vicente, Esther ^a   Solano, Beatriz ^a   Ancizu, Saioa ^a   Pérez Silanes, Silvia ^a   Aldana, Ignacio ^a   Monge, Antonio ^a  

^a UNIVERSITY OF NAVARRA   (Spain)

^b ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

, Unsaturated ketone; 4,5 Dihydro (1H) pyrazole; Anti inflammatory agents; Antioxidant agents; Quinoxaline 1,4 di N oxide

Indexed keywords

3 PHENYL 1 (1,4 DI N OXIDE QUINOXALIN 2 YL) 2 PROPEN 1 ONE DERIVATIVE; 4,5 DIHYDRO (1H) PYRAZOLE DERIVATIVE; CAFFEIC ACID; INDOMETACIN; LIPOXYGENASE; NONSTEROID ANTIINFLAMMATORY AGENT; NORDIHYDROGUAIARETIC ACID; PYRAZOLE DERIVATIVE; QUINOXALINE DERIVATIVE; TOLFENAMIC ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PAW EDEMA; RAT; SOYBEAN; SUBSTITUTION LINE; SUBSTITUTION REACTION;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIOXIDANTS; EDEMA; PYRAZOLES; QUINOXALINES; RATS;

GLYCINE MAX; RATTUS;

EID: 35649010886     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.10.002     Document Type: Article

References (36)

1. Cheeseman G.W.H., and Cookson R.F. In: Weissberger A., and Taylor E.C. (Eds). The Chemistry of Heterocyclic Compounds Vol. 35 (1979), J. Wiley & Sons, New York 1-27 35-38
2. Porter A.E.A. In: Katrizky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon, New York 157-197
3. Balzarini J., De Clercq E., Carbonez A., Burt V., and Kleim J.P. AIDS Res. Hum. Retroviruses 16 6 (2000) 517
4. Musatova I.S., Elina A.S., Padeiskaya E.N., Shipilova L.D., Yakobson G.G., and Furin G.G. Khim. Farm. Zh. 16 (1982) 934
5. Musatova I.S., Elina A.S., and Padeiskaya E.N. Khim. Farm. Zh. 16 (1982) 1063
6. Monge A., Gil M.J., Pascual M.A., and Gastelurrutia M.A. Ann. R. Acad. Farm. 49 (1983) 37
7. Monge A., Gil M.J., and Pascual M.A. Ann. R. Acad. Farm. 49 (1983) 199
8. Ganley B., Chowdhury G., Bhansali J., Daniels J.S., and Gates K.S. Bioorg. Med. Chem. 9 (2001) 2395
9. Monge A., Palop J.A., Lopez de Cerain A., Senador V., Marti{dotless}nez-Crespo F.J., Sainz Y., Narro S., Garci{dotless}a E., de Miguel C., Gonzalez M., Hamilton E., Barker A.J., Clarke E.D., and Greenhow D.T. J. Med. Chem. 38 10 (1995) 1786
10. Monge A., Marti{dotless}nez-Crespo F.J., Lopez de Cerain A., Palop J.A., Narro S., Senador V., Mari{dotless}n A., Sainz Y., Gonzalez M., Hamilton E., and Barker A.J. J. Med. Chem. 38 22 (1995) 4488
11. Monge A., Palop J.A., Gonzalez M., Marti{dotless}nez-Crespo F.J., Lopez de Cerain A., Sainz Y., Narro S., Barrer A.J., and Hamilton E. J. Heterocycl. Chem. 32 (1995) 1213
12. Marti{dotless}nez-Crespo F.J., Palop J.A., Sainz Y., Narro S., Senador V., Gonzalez M., Lopez de Cerain A., Monge A., Hamilton E., and Barker A.J. J. Heterocycl. Chem. 33 (1996) 1671
13. Zarranz B., Jaso A., Aldana I., and Monge A. Bioorg. Med. Chem. 12 (2004) 3711
14. Wood J.G., Johnson J.S., Mattioli L.F., and Gonsalez N.C. J. Appl. Physiol. 87 (1999) 1734
15. Halliwell B., and Gutteridge J.M.C. Methods Enzymol. 186 (1990) 185
16. Garrido G., Gonzalez D., Delporte C., Backhouse N., Quintero G., Nunez-Selles A.J., and Morales M.A. Phytother. Res. 15 (2001) 18
17. Weber V., Coudert P., Rubat C., Duroux E., Vallee-Goyet D., Gardette D., Bria M., Albuisson E., Leal F., Gramain J.-C., Couquelet J., and Madesclaire M. Bioorg. Med. Chem. 10 (2002) 1647
18. Weber V., Rubat C., Duroux E., Lartigue C., Madesclaire M., and Coudert P. Bioorg. Med. Chem. 13 (2005) 4552
19. Nie D., Che M., Grignon D., Tang K., and Honn K.V. Cancer Metastasis Rev. 20 3-4 (2001) 95
20. Honn K.V., Tang D.G., Gao X., Butovich I.A., Liu B., Timar J., and Hagmann W. Cancer Metastasis Rev. 13 3-4 (1994) 365
21. Kelavkar U., Glasgow W., and Eling T.E. Curr. Urol. Rep. 3 3 (2002) 207
22. Shureiqi I., and Lippman S.M. Cancer Res. 61 17 (2001) 6307
23. Nam N.H., Kim Y., You Y.J., Hong D.H., Kim H.M., and Ahn B.Z. Eur. J. Med. Chem. 38 (2003) 179
24. Nielsen S.F., Boesen T., Larsen M., Schonning K., and Kromann H. Bioorg. Med. Chem. 12 (2004) 3047
25. Mamolo M.G., Zampieri D., Falagiani V., Vio L., and Banfi E. Farmaco 56 (2001) 593
26. Jaso A., Zarranz B., Aldana I., and Monge A. Eur. J. Med. Chem. 38 (2003) 791
27. 5 (352.35): C, 64.77; H, 4.54; N, 7.95. Found: C, 64.44; H, 4.83; N, 7.63.
28. Brooks P.M., and Day R.O. N. Eng. J. Med. (1988) 1716
29. Shanbag V.R., Crider M.A., Gohkale R., Harpalani A., and Dick R.M. J. Pharm. Sci. (1992) 149
30. Kontogiorgis C., and Hadjipavlou-Litina D. J. Med. Chem. 48 (2005) 6400
31. Biobyte Corp. 201 West 4th Street, Suite 204 Claremont CA, California 91711, USA.
32. Pontiki E., and Hadjipavlou-Litina D. Med. Chem. 2 3 (2006) 251
33. Edema was induced in the right hind paw of Fisher 344 rats (150-200 g) by the intradermal injection of 0.1 ml of 2% carrageenin in water. Both sexes were used. Females pregnant were excluded. Each group was composed of 6-15 animals. The tested compounds, 0.01 mmol/kg body weight, were suspended in water, with few drops of Tween 80, and ground in a mortar before use and were given intraperitoneally simultaneously with the carrageenin injection.
34. Pontiki E., and Hadjipavlou-Litina D. Mini Rev. Med. Chem. 3 (2003) 487
35. Pontiki E., and Hadjipavlou-Litina D. Curr. Med. Chem. Anti-Inflamm. Anti-Allergy Agents 3 (2004) 139
36. Pontiki E., and Hadjipavlou-Litina D. Med. Res. Rev. 3 (2007) 175