Synthesis and anticonvulsant activity of new N-Mannich bases derived from 5-cyclopropyl-5-phenyl- and 5-cyclopropyl-5-(4-chlorophenyl)-imidazolidine-2,4- diones

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 20, 2011, Pages 6149-6156

  Byrtus, Hanna ^a   Obniska, Jolanta ^a   Czopek, Anna ^a   Kamiński, Krzysztof ^a   Pawłowski, MacIej ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

5 Cyclopropyl 5 phenyl and 5 cyclopropyl 5 (4 chlorophenyl) imidazolidine 2,4 dione; Anticonvulsant activity; Hydantoin; N Mannich bases

Indexed keywords

3 [(3,4 DIHYDRO 1H ISOQUINOLIN 2 YL) METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [(3,4 DIHYDRO 1H ISOQUINOLIN 2 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [(4 BENZOYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [(4 BENZYLOXYCARBONYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [(4 ETHOXYCARBONYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [(4 PHENETHYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [(4 PHENETHYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [(4 PHENYLPIPERAZIN 1 YL)METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [(4 PHENYLPIPERAZIN 1 YL)METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [(MORPHOLIN 4 YL) METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [(MORPHOLIN 4 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [4 (1 PHENYLETHYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [4 (1 PHENYLETHYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [4 (2 METHOXYETHYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [4 (BENZYLOXYCARBONYLPIPERAZIN 1 YL) METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [[4 (2 FLUOROPHENYL)PIPERAZIN 1 YL]METHYL] 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 3 [[4 (2 FLUOROPHENYL)PIPERAZIN 1 YL]METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 3 [[4 (3 PHENYLALLYL) PIPERAZIN 1 YL] METHYL] 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; 5 CYCLOPROPYL 5 (4 CHLOROPHENYL)IMIDAZOLIDINE 2,4 DIONE; 5 CYCLOPROPYL 5 PHENYLIMIDAZOLIDINE 2,4 DIONE; ETHOSUXIMIDE; ETIRACETAM; HYDANTOIN DERIVATIVE; MANNICH BASE; PENTETRAZOLE; PHENYTOIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRIC SHOCK; IN VIVO STUDY; NEUROTOXICITY; NONHUMAN; RAT; ROTAROD TEST; SEIZURE;

ANIMALS; ANTICONVULSANTS; IMIDAZOLIDINES; MALE; MANNICH BASES; MICE; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

MUS; RATTUS;

EID: 80053262138     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.08.017     Document Type: Article

References (31)

1. W. Löscher, and D. Schmidt Epilepsy Res. 69 2006 183
2. J.A. Cramer, S. Mintzer, J. Wheless, and R.H. Mattson Expert Rev. Neurother. 10 2010 885
3. R.S. Greenwood Epilepsia 41 2000
4. M.A. Rogawski Epilepsy Res. 69 2006 273
5. R. Morphy, and Z. Rankovic J. Med. Chem. 48 2005 6523
6. M.G. Wong, J.A. Defina, and P.R. Andrews J. Med. Chem. 29 1986 562
7. S.M. Tasso, L.E. Bruno-Blanch, S.C. Moon, and G.L. Estiú J. Mol. Struct. 504 2000 229
8. L. Bruno-Blanch, J. Gálvez, and R. Garcia-Domenach Bioorg. Med. Chem. Lett. 13 2003 2749
9. 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
10. B. Malawska, and K. Kulig Curr. Opin. Investig. Drugs 6 2005 740
11. M. Bialer, S.I. Johannessen, H.J. Kupferberg, R.H. Levy, E. Perucca, and T. Tomson Epilepsy Res. 73 2007 1
12. J. Obniska, K. Kamiński, A. Dzierawska-Majewska, A. Zagórska, and J. Karolak-Wojciechowska J. Fluorine Chem. 127 2006 417
13. J. Obniska, K. Kamiński, and E. Tatarczyńska Pharmacol. Rep. 58 2006 207
14. J. Obniska, M. Kołaczkowski, B. Duszyńska, and A. Bojarski Eur. J. Med. Chem. 41 2006 874
15. K. Kamiński, and J. Obniska Bioorg. Med. Chem. 16 2008 4921
16. J. Obniska, K. Kamiński, D. Skrzyńska, and J. Pichór Eur. J. Med. Chem. 44 2009 2224
17. J. Obniska, M. Kopytko, A. Zagórska, I. Chlebek, and K. Kamiński Arch. Pharm. Chem. Life Sci. 343 2010 333
18. J. Obniska, H. Byrtus, K. Kamiński, M. Pawłowski, M. Szczesio, and J. Karolak-Wojciechowska Bioorg. Med. Chem. 18 2010 6134
19. J. Obniska, H. Byrtus, A. Czopek, and K. Kamiński Arch. Pharm. Chem. Life Sci. 11 2011 231
20. L.H. Goodson, J.L. Honigberg, J.L. Lehman, and W.H. Burton J. Org. Chem. 25 1960 1920
21. H.S. White Epilepsia 4 2003 2
22. M.A. Rogawski Epilepsy Res. 68 2006 22
23. M.E. Barton, B.D. Klein, H.H. Wolf, and H.S. White Epilepsy Res. 47 2001 217
24. R.L. Krall, J.K. Penry, B.G. White, H.J. Kupferberg, and E.A. Swinyard Epilepsia 19 1978 409
25. H.J. Kupferberg Epilepsia 30 1989 51
26. N.W. Dunham, and T.A. Miya J. Am. Pharm. Assoc. Sci. 46 1957 208
27. W.C. Brown, D.O. Schiffman, E.A. Swinyard, and L.S. Goodman J. Pharmacol. Exp. Ther. 107 1953 273
28. R.F. Kaminski, M.R. Livingood, and M.A. Rogawski Epilepsia 45 2004 864
29. R. Thirumurugan, D. Sriram, A. Saxena, J. Stables, and P. Yogeeswari Bioorg. Med. Chem. 14 2006 3106
30. P. Yogeeswari, D. Sriram, R. Thirumurugan, J.V. Raghavendran, K. Sudhan, P.K. Pavana, and J.P. Stables J. Med. Chem. 48 2005 6202
31. H.S. White, J.H. Woodhead, K.S. Wilcox, J.P. Stables, H.J. Kupferberg, and H.H. Wolf R.H. Levy, R.H. Mattson, B.S. Meldrum, E. Perucca, Antiepileptic Drugs 2002 Lippincott Philadelphia, PA 43 44