Synthesis and investigation of anti-inflammatory activity and gastric ulcerogenicity of novel nitric oxide-donating pyrazoline derivatives

European Journal of Medicinal Chemistry

Volumn 44, Issue 7, 2009, Pages 3068-3076

  Shoman, Mai E ^a   Abdel Aziz, Mohamed ^a   Aly, Omar M ^a   Farag, Hassan H ^b   Morsy, Mohamed A ^c  

^a Minia University   (Egypt)

^b Assiut University   (Egypt)

^c Minia University   (Egypt)

Author keywords

2 Pyrazoline; Anti inflammatory; Gastric toxicity; Nitric oxide

Indexed keywords

1 (2 BROMOACETYL) 4,5 DIHYDRO 5 (2,4 DIMETHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 1 (2 BROMOACETYL) 5 (2 FURYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 1 (2 BROMOACETYL) 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 1 (2 BROMOACETYL) 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (4 METHOXYPHENYL) 1H PYRAZOLE; 1 (2 BROMOPROPIONYL) 4,5 DIHYDRO 5 (2,4 DIMETHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 1 (2 BROMOPROPIONYL) 5 (2 FURYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 1 (2 BROMOPROPIONYL) 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 4,5 DIHYDRO 1 [2 [4 (1 HYDROXYIMINOETHYL)PHENYLAMINO]ACETYL] 5 (2,4 DIMETHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 4,5 DIHYDRO 5 (2,4 DIMETHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1 (2 NITROOXYACETYL) 1H PYRAZOLE; 4,5 DIHYDRO 5 (2,4 DIMETHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1 (2 NITROOXYPROPIONYL) 1H PYRAZOLE; 4,5 DIHYDRO 5 (2,4 DIMETHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 5 (2 FURYL) 4,5 DIHYDRO 1 [2 [4 (1 HYDROXYIMINOETHYL)PHENYLAMINO]ACETYL] 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 5 (2 FURYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1 (2 NITROOXYACETYL) 1H PYRAZOLE; 5 (2 FURYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1 (2 NITROOXYPROPIONYL) 1H PYRAZOLE; 5 (2 FURYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1 (2 NITROOXYACETYL) 1H PYRAZOLE; 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1 (2 NITROOXYPROPIONYL) 1H PYRAZOLE; 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (4 METHOXYPHENYL) 1 (2 NITROOXYACETYL) 1H PYRAZOLE; 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 3 (4 METHOXYPHENYL) 1H PYRAZOLE; ANTIINFLAMMATORY AGENT; INDOMETACIN; NITRIC OXIDE DONOR; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; MALE; NONHUMAN; PAW EDEMA; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STOMACH ULCER;

ANIMALS; ANTI-INFLAMMATORY AGENTS; EDEMA; INDOMETHACIN; MALE; NITRIC OXIDE; PYRAZOLES; RATS; REFERENCE STANDARDS; STOMACH ULCER;

EID: 67349227426     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.07.008     Document Type: Article

References (46)

1. Singh G., and Triadafilopoulos G. J. Rheumatol. Suppl. 56 (1999) 18-24
2. Botting R.M. J. Therm. Biol. 31 (2006) 208-219
3. Naesdal J., and Brown K. Drug Saf. 29 (2006) 119-132
4. Cryer B. Am. J. Gastroenterol. 100 (2005) 1694-1695
5. Lazzaroni M., and Bianchi P.G. Aliment. Pharmacol. Ther. 20 (2004) 48-58
6. James M.W., and Hawkey C.J. Br. J. Clin. Pharmacol. 56 (2003) 146-155
7. Schneider V., Levesque L.E., Zhang B., Hutchinson T., and Brophy J.M. Am. J. Epidemiol. 164 (2006) 881-889
8. Mounier G., Guy C., Berthoux F., Beyens M.N., Ratrema M., and Ollagnier M. Therapie 61 (2006) 255-266
9. Zadrazil J. Vnitr. Lek. 52 (2006) 686-690
10. Adebayo D., and Bjarnason I. Postgrad. Med. J. 82 (2006) 186-191
11. Velázquez C.A., Praveen Rao P.N., Citro M.L., Keefer L.K., and Knaus E.E. Bioorg. Med. Chem. 15 (2007) 4767-4774
12. Wallace J.L., and Miller M.J. Gastroenterology 119 (2000) 512-520
13. Takeuchi K., Yasuhiro T., Asada Y., and Sugawa Y. Digestion 59 (1998) 298-307
14. Holzer P., Pabst M.A., Lipp I.T., Peskar B.M., Livingston E.H., and Guth P.H. Gastroenterol. 98 (1990) 838-848
15. Wallace J.L., Vergnolle N., Muscara M.N., Asfaha S., Chapman K., McKnight W., Del Soldato P., Morelli A., and Fiorucci S. Gastroenterology 117 (1999) 557-566
16. Brown J.F., Keates A.C., Hanson P.J., and Whittle B.J. Am. J. Physiol. Gastrointest. Liver Physiol. 265 (1993) G418-G422
17. Holm M., Johansson B., Petterssson A., and Fandrisk L. Acta Physiol. Scand. 162 (1998) 461-468
18. Iwata F., and Leung F.W. Am. J. Physiol. Gastrointest. Liver Physiol. 268 (1995) G153-G160
19. Fujihara C.K., Malheiros D.M., Donato J.L., Poli A., De Nucci G., and Zatz R. Am. J. Physiol. Renal Physiol. 274 (1998) F573-F579
20. Karthikeyan M.S., Holla B.S., and Kumari N.S. Eur. J. Med. Chem. 42 (2007) 30-36
21. Zitouni G.T., Özdemir A., and Gu{combining double acute accent}ven K. Arch. Pharm. 338 (2005) 96-104
22. Zitouni G.T., Özdemir A., Kaplancikli Z.A., Chevallet P., and Tunali Y. Phosphorus Sulfur Silicon Relat. Elem. 180 (2005) 2717-2724
23. Barsoum F.F., Hosnib H.M., and Girgis A.S. Bioorg. Med. Chem. 14 (2006) 3929-3937
24. Rani P., Srivastava V.K., and Kumar A. Eur. J. Med. Chem. 39 (2004) 449-452
25. Bansal E., Srivastava V.K., and Kumar A. Eur. J. Med. Chem. 36 (2001) 81-92
26. Zitouni G.T., Chevallet P., Kiliç F.S., and Erol K. Eur. J. Med. Chem. 35 (2000) 635-641
27. Jeong T.S., Kim K.S., An S.J., Cho K.H., Lee S., and Lee W.S. Bioorg. Med. Chem. Lett. 14 (2004) 2715-2717
28. Jeong T.S., Kim K.S., Kim J.R., Cho K.H., Lee S., and Lee W.S. Bioorg. Med. Chem. Lett. 14 (2004) 2719-2723
29. Palaska E., Erol D., and Demirdamar R. Eur. J. Med. Chem. 31 (1996) 43-47
30. Soni N., Pande K., Kalsi R., Gupta T.K., Parmer S.S., and Barthwal J.P. Res. Commun. Chem. Pathol. Pharmacol. 56 (1987) 129-132
31. Winter C.A., Risely E.A., and Nuss G.W. Proc. Soc. Exp. Biol. Med. 111 (1962) 544-547
32. Nojima H., Tsuneki H., Kimura I., and Kimura M. Br. J. Pharmacol. 116 (1995) 1680-1684
33. Cocco M.T., Congiu C., Onnis V., Morelli M., Felipo V., and Cauli O. Bioorg. Med. Chem. 12 (2004) 4169-4177
34. De Andrade S.F., Lemosa M., Comunello E., Noldin V.F., Filho V.C., and Niero R. J. Ethnopharmacol. 113 (2007) 252-257
35. Lolli M.L., Cena C., Medana C., Lazzarato L., Morini G., Coruzzi G., Manarini S., Fruttero R., and Gasco A. J. Med. Chem. 44 (2001) 3463-3468
36. Velazquez C.A., Rao P.N.P., McDonald R., and Knaus E.E. Bioorg. Med. Chem. 13 (2005) 2749-2757
37. Perini R., Fiorucci S., and Wallace J.L. Can. J. Gastroenterol. 18 (2004) 229-236
38. Bastaki S.M., and Wallace J.L. Can. J. Gastroenterol. 13 (1999) 123-127
39. Bhat B.A., Dhar K.L., Puri S.C., Saxena A.K., Shanmugavel M., and Qazi G.N. Bioorg. Med. Chem. Lett. 15 (2005) 3177-3180
40. Imran M., Alam O., Siddiqqui N., and Khan S.A. J. Pharm. Res. 4 (2005) 75-79
41. Pop E., Wu W.M., Shek E., and Bodor N. Drug Des. Deliv. 5 (1989) 93-115
42. Kokotos G. Synthesis (1990) 299-301
43. López G.V., Batthyány C., Blanco F., Botti H., Trostchansky A., Migliaro E., Radi R., González M., Cerecetto H., and Rubbo H. Bioorg. Med. Chem. 13 (2005) 5787-5796
44. Srivastava V.K., and Kumar A. Bioorg. Med. Chem. 12 (2004) 1257-1264
45. Abadi A.H., Hegazy G.H., and El-Zaher A.A. Bioorg. Med. Chem. 13 (2005) 5759-5765
46. Tsikas D. J. Chromatogr. B 851 (2007) 51-70