In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 13, 2009, Pages 4336-4344

  De Wael, Frederic ^a   Jeanjot, Paul ^a   Moens, Cédric ^a   Verbeuren, Tony ^b   Cordi, Alex ^b   Bouskela, Eliete ^c   Rees, Jean François ^a   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b INSTITUT DE RECHERCHES SERVIER   (France)

^c STATE UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Aminopyrazine; Antioxidant; Imidazopyrazinone; Ischemia reperfusion

Indexed keywords

2 AMINO 3 (4 FLUOROPHENYL) 5 (4 HYDROXYPHENYL) 1,4 PYRAZINE; 2 AMINO 3 (4 N,N DIMETHYLAMINOPHENYL) 5 (4 HYDROXYPHENYL) 1,4 PYRAZINE; 2 METHYL 6 (4 HYDROXYPHENYL) 8 (4 METHOXYPHENYL) 3,7 DIHYDROIMIDAZO[1,2 A]PYRAZIN 3 ONE; ANTIOXIDANT; BICYCLO COMPOUND; IMIDE; KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BLOOD VESSEL INJURY; CONTROLLED STUDY; DEGRADATION; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; ISCHEMIA; MALE; NONHUMAN; REPERFUSION INJURY; STRUCTURE ACTIVITY RELATION; SYRIAN HAMSTER;

AMINES; ANIMALS; ANTIOXIDANTS; CAPILLARY PERMEABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; IMIDAZOLES; ISCHEMIA; MALE; OXIDATION-REDUCTION; PYRAZINES; REPERFUSION INJURY;

EID: 66449109549     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.025     Document Type: Article

References (46)

1. In: Sies H. (Ed). Oxidative Stress: Oxidants and Antioxidants (1991), Academic Press, London
2. In: Rice-Evans C.A., and Burdon C.A. (Eds). Free Radicals Damage and its Control (New Comprehensive Biochemistry) Vol. 28 (1994), Elsevier, Amsterdam
3. In: Halliwell B., and Gutteridge J.M.C. (Eds). Free Radicals in Biology and Medicine (1999), Oxford University Press, Oxford
4. Beckman K.B., and Ames B.N. Physiol. Rev. 78 (1998) 547-581
5. Morrissey P.A., and O'Brien N.M. Int. Dairy J. 8 (1998) 463-472
6. Krishna M.C., De Graff W., Hankovzsky O.H., Sar C.P., Kalai T., Jeko T., Russo A., Mitchell J.B., and Hideg K. J. Med. Chem. 41 (1998) 3477
7. Schackelfold R.E., Kaufmann W.K., and Paules R.S. Free Radical Biol. Med. 28 (2000) 1387
8. Kehrer J.P. Toxicology 149 (2000) 43
9. In: Scoot G. (Ed). Antioxidants in Science, Technology, Medicine and Nutrition (1997), Albion Publishing Ltd, Chichester
10. In: Frei B. (Ed). Natural Antioxidants in Human Health and Disease (1994), Academic Press, San Diego
11. Larson R.A. Naturally Occurring Antioxidants (1997), Lewis CRC Press, Boca Raton
12. In: Packer L., and Cadenas E. (Eds). Handbook of Synthetic Antioxidants (1997), Marcel Dekker, New York
13. Andersson C.-M., Hallberg A., and Hogberg A. Adv. Drug Res. 28 (1996) 65
14. Gordon M.H. Natural products reports (1996) 265
15. Teranishi K. Bioorg. Chem. 35 (2007) 82
16. Wu C., Kawasaki K., Ohgiya S., and Ohmiya Y. Tetrahedron Lett. 47 (2006) 753
17. Auld D.S., Southall N.T., Jadhav A., Jhonson R.L., Diller D.J., Simeonov A., Austin C.P., and Inglese J. J. Med. Chem. 51 (2008) 2372
18. Kuse M., and Isobe M. Tetrahedron 56 (2000) 2629
19. Vysotski E.S., and Lee J. Acc. Chem. Res. 37 (2004) 405
20. Kotarsky K., Antonsson L., Owman C., and Olde B. Anal. Biochem. 316 (2003) 208
21. Alvarez J., and Montero M. Cell Calcium 32 (2002) 251
22. Teranishi K., and Shimomura O. Anal. Biochem. 249 (1997) 37
23. Daiber A., August M., Baldus S., Wendt M., Oelze M., Sydow K., Kleschyov A.L., and Munzel T. Free Radical Biol. Med. 36 (2004) 101
24. Dubuisson M.L.N., Rees J.-F., and Marchand-Brynaert J. Drug Dev. Ind. Pharm. 31 (2005) 827
25. Dubuisson M.L.N., Rees J.-F., and Marchand-Brynaert J. Mini-Rev. Med. Chem. 4 (2004) 421
26. Janssens B., Le-Gall R., and Rees J.-F. J. Fish Biol. 61 (2002) 71
27. Takahashi Y., Kondo H., Maki S., Niwa H., Ikeda H., and Hirano T. Tetrahedron Lett. 47 (2006) 6057
28. Kondo H., Igarashi T., Maki S., Niwa H., Ikeda H., and Hirano T. Tetrahedron Lett. 46 (2005) 7701
29. Usami K., and Isobe M. Tetrahedron 52 (1996) 12061
30. Shimomura O., and Johnson F.H. Biochem. Biophys. Res. Commun. 44 (1971) 340
31. 2H).
32. Devillers I., Dive G., De Tollenaere C., Falmagne B., de Wergifosse B., Rees J.-F., and Marchand-Brynaert J. Bioorg. Med. Chem. Lett. 11 (2001) 2305
33. Hirano T., Nishibuchi S., Yoneda M., Tsujimoto K., and Ohashi M. Tetrahedron 49 (1993) 9267
34. Cavalier J.-F., Burton M., De Tollenaere C., Dussart F., Marchand C., Rees J.-F., and Marchand-Brynaert J. Synthesis 5 (2001) 768
35. Cavalier J.-F., Burton M., Dussart F., Marchand C., Rees J.-F., and Marchand-Brynaert J. Bioorg. Med. Chem. 9 (2001) 1037
36. Jeanjot P., Bruyneel F., Arrault A., Gharbi S., Cavalier J.-F., Abels A., Marchand C., Touillaux R., Rees J.-F., and Marchand-Brynaert J. Synthesis 4 (2003) 513
37. -1, according to: Achord, J. M.; Hussey, C. L. Anal. Chem. 1980, 52, 601. Non-dried solvents were used, thus containing enough moisture for performing the hydrolysis of highly reactive intermediates.
38. Burton M., De Tollenaere C., Cavalier J.-F., Marchand C., Dussart F., Rees J.-F., and Marchand-Brynaert J. Free Radical Res. 37 (2003) 145
39. Goto T., and Fukatsu H. Tetrahedron Lett. 10 (1969) 4299
40. Teranishi K., Tanabe S., Hisamatsu M., and Yamada T. Luminescence 14 (1999) 303
41. Teranishi K., Nishiguchi T., and Ueda H. Carbohydr. Res. 228 (2003) 987
42. Adamczyk M., Akireddy S.R., Johnson D.D., Mattingly P.G., Pan Y., and Reddy R.E. Tetrahedron 59 (2003) 8129
43. 30,31
44. Arrault A., Dubuisson M.L.N., Gharbi S., Marchand C., Verbeuren T., Rupin A., Cordi A., Bouskela E., Rees J.-F., and Marchand-Brynaert J. Bioorg. Med. Chem. Lett. 13 (2003) 653
45. Newan D.J. J. Med. Chem. 51 (2008) 2589
46. For a recent review on dual action approaches, see:. Bremner J.B., Ambrus J.I., and Samosorn S. Curr. Med. Chem. 14 (2007) 1459