Isoxazole substituted chromans against oxidative stress-induced neuronal damage

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 16, 2011, Pages 4841-4850

  Koufaki, Maria ^a   Tsatsaroni, Alexandra ^a   Alexi, Xanthippi ^a   Guerrand, Helne ^a   Zerva, Sofia ^a   Alexis, Michael N ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

Author keywords

Antioxidants; Chromans; Click chemistry; Isoxazoles; Neuronal damage; Oxidative stress

Indexed keywords

2 [5 (3,4 DIHYDRO 6 HYDROXY 2,2,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 5 YL)ISOXAZOL 3 YL] 3,4 DIHYDRO 2,5,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL; 2 [[[3 (4 METHOXYPHENYL)ISOXAZOL 5 YL]METHYOXY]METHYL] 2,5,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL; 2 [[[3 (PHENYL)ISOXAZOL 5 YL]METHYOXY]METHYL] 2,5,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 (3 PHENYLISOXAZOL 5 YL) 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 (5 PHENYLISOXAZOL 3 YL) 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 (5 PROPYLISOXAZOL 3 YL) 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 [3 (4 NITROPHENYL)ISOXAZOL 5 YL] 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 [5 (4 HYDROXYPHENYL)ISOXAZOL 3 YL] 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 [5 (4 METHOXYPHENYL)ISOXAZOL 3 YL] 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 5 [5 (4 NITROPHENYL)ISOXAZOL 3 YL] 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,5,7,8 TETRAMETHYL 2 (3 PHENYL 5 ISOXAZOLYL) 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,5,7,8 TETRAMETHYL 2 (5 PHENYL 3 ISOXAZOLYL) 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,5,7,8 TETRAMETHYL 2 [3 (4 METHOXYPHENYL)ISOXAZOL 5 YL] 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 2,5,7,8 TETRAMETHYL 2 [5 (4 METHOXYPHENYL) 3 ISOXAZOLYL] 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 5 [3 (4 FLUOROPHENYL)ISOXAZOL 5 YL] 2,2,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 5 [3 (4 HYDROXYPHENYL)ISOXAZOL 5 YL] 2,2,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL; 3,4 DIHYDRO 5 [3 (4 METHOXYPHENYL)ISOXAZOL 5 YL] 2,2,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL; 5 (3,4 DIHYDRO 6 METHOXY 2,2,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 5 YL) 3 PHENYLISOXAZOLE; 5 [[(3,4 DIHYDRO 6 METHOXY 2,5,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 2 YL)METHOXY]METHYL] 3 (4 HYDROXYPHENYL)ISOXAZOLE; 5,5' (ISOXAZOLE 3,5 DIYL)BIS(3,4 DIHYDRO 2,2,7,8 TETRAMETHYL 2H 1 BENZOPYRAN 6 OL); CHROMAN DERIVATIVE; ISOXAZOLE DERIVATIVE; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CYCLOADDITION; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MOUSE; NERVE CELL LESION; NEUROPROTECTION; NONHUMAN; OXIDATIVE STRESS; STRUCTURE ACTIVITY RELATION;

ANIMALS; CATECHOLS; CELL DEATH; CHROMANS; DRUG EVALUATION, PRECLINICAL; HIPPOCAMPUS; HUMANS; ISOXAZOLES; MICE; NEURONS; NEUROPROTECTIVE AGENTS; OXIDATIVE STRESS;

EID: 79961166710     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.074     Document Type: Article

References (33)

1. J.-M. Zingg Mol. Aspects Med. 28 2007 400
2. R. Brigelius-Flohé Free Radic. Biol. Med. 46 2009 543
3. Z.P. Xiao, Z.Y. Peng, M.J. Peng, W.B. Yan, Y.Z. Ouyang, and H.L. Zhu Mini-Rev. Med. Chem. 11 2011 169
4. H. Cerecetto, and G.V. López Mini-Rev. Med. Chem. 7 2007 315
5. H.C. Shen Tetrahedron 65 2009 3931
6. M. Koufaki, T. Calogeropoulou, A. Detsi, A. Roditis, A. Kourounakis, P. Papazafiri, K. Tsiakitzis, C. Gaitanaki, I. Beis, and P. Kourounakis J. Med. Chem. 44 2001 4300
7. M. Koufaki, T. Calogeropoulou, E. Rekka, M. Chryselis, P. Papazafiri, C. Gaitanaki, and A. Makriyannis Bioorg. Med. Chem. 11 2003 5209
8. M. Koufaki, A. Detsi, E. Theodorou, C. Kiziridi, T. Calogeropoulou, A. Vassilopoulos, A. Kourounakis, E. Rekka, P. Kourounakis, C. Gaitanaki, and P. Papazafiri Bioorg. Med. Chem. 12 2004 4835
9. M. Koufaki, C. Kiziridi, P. Papazafiri, A. Vassilopoulos, A. Varró, Z. Nagy, A. Farkas, and A. Makriyannis Bioorg. Med. Chem. 14 2006 6666
10. M. Koufaki, E. Theodorou, D. Galaris, L. Nousis, E.S. Katsanou, and M.N. Alexis J. Med. Chem. 49 2006 300
11. M. Koufaki, C. Kiziridi, X. Alexi, and M.N. Alexis Bioorg. Med. Chem. 17 2009 6432
12. M. Koufaki, E. Theodorou, X. Alexi, and M.N. Alexis Bioorg. Med. Chem. 18 2010 3898
13. P.G. Nantermet, J.C. Barrow, G.F. Lundell, J.M. Pellicore, K.E. Rittle, M.B. Young, R.M. Freidinger, T.M. Connolly, C. Condra, J. Karczewski, R.A. Bednar, S.L. Gaul, R.J. Gould, K. Prendergast, and H.G. Selnick Bioorg. Med. Chem. Lett. 12 2002 319
14. V.E. Kuz'min, A.G. Artemenko, E.N. Muratov, I.L. Volineckaya, V.A. Makarov, O.B. Riabova, P. Wutzler, and M. Schmidtke J. Med. Chem. 50 2007 4205
15. D. Simoni, R. Rondanin, R. Baruchello, M. Rizzi, G. Grisolia, M. Eleopra, S. Grimaudo, A. Di Cristina, M.R. Pipitone, M.R. Bongiorno, M. Aric, F.P. Invidiata, and M. Tolomeo J. Med. Chem. 51 2008 4796
16. A. Lilienkampf, M. Pieroni, B. Wan, Y. Wang, S.G. Franzblau, and A.P. Kozikowski J. Med. Chem. 53 2010 678
17. T.V. Hansen, P. Wu, and V.V. Fokin J. Org. Chem. 70 2005 7761
18. K. Vukics, A. Koenczoel, A. Kis-Varga, A. Gere, and J. Fischer Bioorg. Med. Chem. Lett. 15 2005 3012
19. S. Ohira Synth. Commun. 19 1989 561
20. S. Muller, B. Liepold, G.J. Roth, and H.J. Bestmann Synth. Lett. 1996 521
21. S. Couve-Bonnaire, D.T.H. Chou, Z. Gan, and P. Arya J. Comb. Chem. 6 2004 73
22. A.R. Katritzky, C. Chassaing, S.J. Barrow, Z. Zhang, V. Vvedensky, and B. Forood J. Comb. Chem. 4 2002 249
23. R.S. Garigipati, B. Adams, J.L. Adams, and S.K. Sarkar J. Org. Chem. 61 1996 2911
24. J.Y. Hwang, H.-S. Choi, J. Seo, H.J. La, D.-S. Kim, H.S. Jeon, M.-K. Jeon, D.-H. Lee, and Y.-D. Gong J. Org. Chem. 70 2005 10151
25. S. Tan, D. Schubert, and P. Maher Curr. Top. Med. Chem. 6 2001 497
26. P. Albrecht, J. Lewerenz, S. Dittmer, R. Noack, P. Maher, and A. Methner CNS Neurol. Disord. Drug Targets 9 2010 373
27. M. Fukui, J.-H. Song, J. Choi, H.J. Choi, and B.T. Zhu Eur. J. Pharmacol. 617 2009 1
28. Y. Liu, and D.R. Schubert J. Biomed. Sci. 16 2009 98
29. P. Maher, K.F. Salgado, J.A. Zivin, and P.A. Lapchak Brain Res. 1173 2007 117
30. E. Perez, R. Liu, S.H. Yang, Z.Y. Cai, D.F. Covey, and J.W. Simpkins Brain Res. 1038 2005 216
31. Y. Saito, K. Nishio, Y.O. Akazawa, K. Yamanaka, A. Miyama, Y. Yoshida, N. Noguchi, and E. Niki Free Radic. Biol. Med. 49 2010 1542
32. S.H. Yang, S.N. Sarkar, R. Liu, E.J. Perez, X. Wang, Y. Wen, L.J. Yan, and J.W. Simpkins J. Biol. Chem. 284 2009 9540
33. C. Villalonga-Barber, A.K. Meligova, X. Alexi, B.R. Steele, C.E. Kouzinos, C.G. Screttas, E.S. Katsanou, M. Micha-Screttas, and M.N. Alexis Bioorg. Med. Chem. 19 2011 339