Design and synthesis of new of 3-(benzo[d]isoxazol-3-yl)-1-substituted pyrrolidine-2, 5-dione derivatives as anticonvulsants

European Journal of Medicinal Chemistry

Volumn 84, Issue , 2014, Pages 42-50

  Malik, Sachin ^a   Ahuja, Priya ^a   Sahu, Kapendra ^a   Khan, Suroor Ahmad ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

Anticonvulsant activity; Benzisoxazole; Pyrrolidine 2, 5 dione; Quantification studies

Indexed keywords

3 (BENZO[D]ISOXAZOL 3 YL) 1 (4 CHLOROPHENYL) PYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 (4 FLUOROPHENYL) PYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 (4 METHOXYPHENYL) 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 (PYRIDIN 2 YL) PYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 (PYRIDIN 3 YL) PYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 (PYRIDIN 4 YL) PYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 BUTYLPYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 CYCLOHEXYLPYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 ETHYLPYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 PHENYLPYRROLIDINE 2,5 DIONE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 PROPYLPYRROLIDINE 2,5 DIONE; ANTICONVULSIVE AGENT; ETHOSUXIMIDE; PENTETRAZOLE; PHENYTOIN; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; 3-(BENZO(D)ISOXAZOL-3-YL)-1-(4-FLUOROPHENYL)PYRROLIDINE-2,5-DIONE; 3-(BENZO(D)ISOXAZOL-3-YL)-1-CYCLOHEXYLPYRROLIDINE-2,5-DIONE; ISOXAZOLE DERIVATIVE; SUCCINIMIDE DERIVATIVE; 3 (BENZO[D]ISOXAZOL 3 YL) 1 (4 METHOXYPHENYL) PYRROLIDINE 2,5 DIONE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG PENETRATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ELECTRIC SHOCK; IN VIVO STUDY; MOTOR DYSFUNCTION; MOUSE; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; QUANTITATIVE ANALYSIS; RAT; ROTAROD TEST; SEIZURE; SEIZURE THRESHOLD; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MOTOR ACTIVITY; SEIZURES; SYNTHESIS; WISTAR RAT; DRUG EFFICACY; EPILEPSY; EXPERIMENTAL TEST; MAXIMAL ELECTROSHOCK TEST; NUCLEAR MAGNETIC RESONANCE; PENTYLENETETRAZOLE SEIZURE TEST;

ANIMALS; ANTICONVULSANTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ELECTROSHOCK; ISOXAZOLES; MICE; MOLECULAR STRUCTURE; MOTOR ACTIVITY; PENTYLENETETRAZOLE; RATS; RATS, WISTAR; SEIZURES; STRUCTURE-ACTIVITY RELATIONSHIP; SUCCINIMIDES;

EID: 84904019397     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.07.016     Document Type: Article

References (44)

1. B.S. Chang, and D.H. Lowenstein N. Engl. J. Med. 349 2003 1257 1266
2. B.S. Meldrum, and C.J. Bruton Epilepsy J.H. Adams, L.W. Duchen, Greenfield's Neuropathology 1992 Oxford University Press New York 1246 1283
3. M.J. Eadie Drugs 27 1984 328 363
4. I.E. Leppik Epilepsia 35 1994 29 40
5. M. Brodie Lancet 339 1992 1397 1400
6. M.L. Wagner Am. J. Hosp. Pharm. 51 1994 1657 1666
7. G.A.B. Davies-Jones Anticonvulsants: Side Effects of Drugs eleventh ed. 1988 Elsevier Science New York
8. D.T. Barkmeier, and J.A. Loeb Clin. EEG Neurosci. 40 2009 234 238
9. M.G. Wong, J.A. Defina, and P.R. Andrews J. Med. Chem. 29 1986 562 572
10. L. Bruno-Blanch, J. Galvez, and R. Garcia-Domenach Bioorg. Med. Chem. Lett. 13 2003 2749 2754
11. B.M. Kenda, A.C. Matagne, P.E. Talaga, P.M. Pasau, E. Differding, B.I. Lallemand, A.M. Frycia, F.G. Moureau, H.V. Klitgaard, M.R. Gillard, B. Fuks, and P. Michel J. Med. Chem. 47 2004 530 549
12. M. Bialer, S.I. Johannessen, H.J. Kupferberg, R.H. Levy, E. Perucca, and T. Tomson Epilepsy Res. 73 2007 1 52
13. B. Malawska, and K. Kulig Curr. Opin. Investig. Drugs 6 2005 740 746
14. B. Bennett, A. Matagne, P. Michel, M. Leonard, M. Cornet, M.A. Meeus, and N. Toublanc Neurotherapeutics 4 2007 117 122
15. M.A. Rogawski Epilepsy Res. 68 2006 22 28
16. J. Obniska, and A. Zagórska Il Fram. 58 2003 1227 1234
17. J. Obniska, K. Kaminski, D. Skrzynska, and J. Pichor Eur. J. Med. Chem. 44 2009 2224 2233
18. J. Obniska, M. Kopytko, A. Zagorska, I. Chlebek, and K. Kaminski Arch. Pharm. Chem. Life Sci. 343 2010 333 341
19. J. Obniska, H. Byrtus, K. Kaminski, M. Pawlowski, M. Szczesio, and J. Karolak-Wojciechowska Bioorg. Med. Chem. 16 2010 6134 6142
20. J. Obniska, I. Chlebek, K. Kaminski, and J. Karolak-Wojciechowska Arch. Pharm. Weinh. 349 2013 71 82
21. K. Kaminski, J. Obniska, I. Chlebek, B. Wiklik, and S. Rzepka Bioorg. Med. Chem. 21 2013 6821 6830
22. J. Obniska, I. Chlebek, and K. Kaminski Arch. Pharm. Weinh. 345 2012 713 722
23. K. Kaminski, S. Rzepka, and J. Obniska Bioorg. Med. Chem. Lett. 21 2011 5800 5803
24. M. Bialer, S.I. Johannessen, H.J. Kupferberg, R.H. Levy, P. Loiseau, and E. Perucca Epilepsy Res. 51 2002 31 71
25. T.R. Henry, I. Leppik, R.J. Gumnit, and M. Jacobs Neurology 38 1988 928 931
26. J.C. Sackellares, P.D. Donofrio, J.G. Wagner, B. Abou- Khalil, S. Berent, and K. Aasved-Hoyt Epilepsia 26 1985 206 211
27. M. Seino, H. Miyzaki, and T. Ito Zonisamide F. Pisani, E. Perucca, G. Avanzini, A. Richens, New Antiepileptic Drugs 1991 Elsevier Science Amsterdam 169 174 (Epilepsy Res., Suppl. 3)
28. Y. Suzuki, T. Magai, J. Ono, K. Imai, K. Ostani, T. Tagawa, J. Abe, M. Shiomi, and S. Okada Epilepsia 38 1997 1035 1038
29. G. Zaccara, and L.M. Specchio Neuropsychiatr. Dis. Treat. 5 2009 249 259
30. M.A. Rogawski, and W. Losher Nat. Rev. Neurosci. 5 2004 553 564
31. H. Uno, M. Kurokawa, Y. Masuda, and H. Nishimura J. Med. Chem. 22 1979 180 183
32. C. Dollery Therapeutic Drugs second ed. 1999 Churchill Livingstone Edinburgh, UK
33. H.S. White, J.H. Woodhead, K.S. Wilcox, J.P. Stables, H.J. Kupferberg, and H.H. Wolf Discovery and preclinical development of antiepileptic drugs R.H. Levy, R.H. Mattson, B.S. Meldrum, E. Perucca, Antiepileptic Drugs 2002 Lippincott Philadelphia 36 48
34. H.S. White Epilepsia 44 2003 2 8
35. R. Thirumurugan, D. Sriram, A. Saxena, J.P. Stables, and P. Yogeeswari Bioorg. Med. Chem. 14 2006 3106 3112
36. P. Yogeeswari, D. Sriram, R. Thirumurugan, J.V. Raghavendran, K. Sudhan, R.K. Pavana, and J.P. Stables J. Med. Chem. 48 2005 6202 6211
37. R.J. Porter, J.J. Cereghino, G.D. Gladding, B.J. Hessie, H.J. Kupferberg, B. Scoville, and B.G. White Clevel. Clin. Q. 51 1984 293 305
38. J.R. Dimmock, S.N. Pandeya, J.W. Quail, T.M. Allen, and G.Y. Kao Eur. J. Med. Chem. 30 1995 303 314
39. E.A. Swinyard, J.H. Woodhead, H.S. White, and M.R. Franklin General principles: experimental selection, quantification, and evaluation of anticonvulsants R.H. Levy, R.H.M. Melrum, J.K. Penry, F.E. Dreifuss, Antiepileptic Drugs 1989 Raven Press New York 43 44
40. H.S. White, M. Johnson, H.H. Wolf, and H.J. Kupferberg Ital. J. Neurol. Sci. 16 1995 73 77
41. C.R. Clark, M.J.M. Wells, R.T. Sansom, G.N. Norris, R.C. Dockens, and W.R. Ravis J. Med. Chem. 27 1984 779 782
42. N.W. Dunham, and T.A. Miya J. Am. Pharm. Assoc. Sci. 46 1957 208 209
43. H.G. Vogel Drug Discovery and Evaluation - Pharmacological Assays 2002 Springer Germany 487 493
44. M.L. Brown, C.C. Zha, C.C. Van Dyke, G.B. Brown, and W.J. Brouillette J. Med. Chem. 75 1999 1537 1545