Synthesis and anticonvulsant activity of some ω-(1H-imidazol-1-yl)-N- phenylacetamide and propionamide derivatives

Farmaco

Volumn 59, Issue 8, 2004, Pages 595-600

  Soyer, Zeynep ^a   Kiliç, Fatma Sultan ^b   Erol, Kevser ^b   Pabuçcuoglu, Varol ^a  

^a EGE UNIVERSITY   (Turkey)

^b ESKISEHIR OSMANGAZI UNIVERSITY   (Turkey)

Author keywords

Anilide; Anticonvulsant; Imidazole; MES; Rotamer

Indexed keywords

2 (1H IMIDAZOL 1 YL) N (2 CHLOROPHENYL)ACETAMIDE; ACETAMIDE DERIVATIVE; ANTICONVULSIVE AGENT; OMEGA (1H IMIDAZOL 1 YL) N PHENYLACETAMIDE; PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRIC SHOCK; INFRARED SPECTROSCOPY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

ACETAMIDES; AMIDES; ANIMALS; ANTICONVULSANTS; DRUG EVALUATION, PRECLINICAL; ELECTROSHOCK; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; MOLECULAR STRUCTURE; SEIZURES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 3242710377     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2003.07.011     Document Type: Article

References (25)

1. Löscher W. New visions in the pharmacology of anticonvulsion. Eur. J. Pharmacol. 342:1998;1-13
2. Lin Z., Kadaba P.K. Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents. Med. Res. Rev. 17:1997;537-572
3. Brodie M.J. Do we need any more new antiepileptic drugs. Epilepsy Res. 45:2001;3-6
4. Ho B., Venkatarangan M.P., Cruse F.S., Hinko N.C., Andersen H.P., Crider M.A., et al. Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsant. Eur. J. Med. Chem. 33:1998;23-31
5. Lepage F., Tombret F., Cuvier G., Marivain A., Gillardin J.M. New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents. Eur. J Med. Chem. 27:1992;581-593
6. Clark C.R., Lin C.M., Sansom T. Anticonvulsant activity of some 2- and 3-aminobenzanilides. J. Med. Chem. 29:1986;1534-1537
7. Clark C.R., Sansom R.T., Lin C.M., Norris G.N. Anticonvulsant activity of some 4-aminobenzanilides. J. Med. Chem. 28:1985;1259-1262
8. Clark C.R., Wells M.J.M., Sansom R.T., Norris G.N., Dockens R.C., Ravis W.R. Anticonvulsant activity of some 4-aminobenzamides. J. Med. Chem. 27:1984;779-782
9. Bailleux V., Vallée L., Nuyts J.P., Hamoir G., Poupaert H.J., Stables J.P., et al. Synthesis and anticonvulsant activity of some 4-nitro-N-phenylbenzamides. Eur. J. Med Chem. 30:1995;439-444
10. Diouf O., Bourhim M., Lambert D.M., Poupaert J.H., Stables J.P., Vamecq V. Anticonvulsant and neurotoxicological properties of 4-amino-(2-ethylphenyl) benzamide, a potent ameltolide analogue. Biomed. Pharmacother. 51:1997;131-136
11. Bourhim M., Poupaert J.H., Stables J.P., Vallée L., Vamecq J. Design, anticonvulsive and neurotoxic properties of retrobenzamides. Arzneim. Forsch./Drug Res. 49:(I):1999;81-87
12. Vamecq J., Bac P., Herrenknecht C., Maurois P., Delcourt P., Stables J.P. Synthesis and anticonvulsant and neurotoxic properties of substituted N-phenyl derivatives of the phthalimide pharmacophore. J. Med. Chem. 43:2000;1311-1319
13. Bailleux V., Vallée L., Nuyts J.P., Vamecq J. Anticonvulsant activity of some 4-amino-N-phenylphthalimides and N-(3-amino-2-methylphenyl) phthalimides. Biomed. Pharmacother. 48:1994;95-101
14. Bailleux V., Vallée L., Nuyts J.P., Vamecq J. Synthesis and anticonvulsant activity of some N-phenylphthalimides. Chem. Pharm. Bull. 42:1994;1817-1821
15. Poupaert J.H., Hamoir G., Barbeaux P., Lambert D., Henichart J.P. Anticonvulsant activity of some N-phenylphthalimide derivatives in rats and mice. J. Pharm. Pharmacol. 47:1995;89-91
16. Clark C.R. Comparative anticonvulsant activity and neurotoxicity of 4-amino-N-(2,6-dimethylphenyl)benzamide and prototype antiepileptic drugs in mice and rats. Epilepsia. 29:1988;198-203
17. Leppik I.O. Antiepileptic drugs in development: prospects for the near future. Epilepsia. 35:1994;S29-S40
18. Bailleux V., Vallée L., Nuyts J.P., Hamoir G., Poupaert H.J., Stables J.P., et al. Comparative anticonvulsant activity and neurotoxicity of 4-amino-N-(2,6-dimethylphenyl)phthalimide and prototype antiepileptic drugs in mice and rats. Epilepsia. 36:1995;559-565
19. Akturk Z., Kilic F., Erol K., Pabuccuoglu V. Synthesis and anticonvulsant activity of some ω-(1H-1-imidazolyl)-N-phenylalkanoic acid amide derivatives. Il Farmaco. 57:2002;201-206
20. Özkanli F., Dalkara S., Çaliş Ü, Wilke A. Synthesis of some N-arylazole acetamide derivatives and their anticonvulsant and antimicrobial activities. Arzneim. Forsch./Drug Res. 44:1994;920-924
21. Di Gangi F.E. Synthesis of some beta-dialkylaminopropioanilides. J. Am. Chem. Soc. XLIV:1955;135-137
22. Ucar H., Derpoorten K.V., Cacciaguerra S., Spampinato S., Stables J.P., Depovere P., et al. Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives. J. Med. Chem. 41:1998;1138-1145
23. Curran D.P., Hale G.R., Geib S.J., Balog A., Cass Q.B., Degani A.L.G., et al. Rotational features of carbon-nitrogen bonds in axially chiral o-tert-butyl anilides and related molecules. Potential substrates for the 'prochiral auxiliary' approach to asymmetric synthesis. Tetrahed. Asymmet. 8:1997;3955-3975
24. Hesse M., Meier H., Zeeh B. Spectroscopic Methods in Organic Chemistry. 1997;88-94 Georg Thieme Verlag, Stuttgart, New York
25. Richard S.S. Laboratory Guide to Proton NMR Spectroscopy. 1988;101-105 Blackwell Scientific Publications, Oxford-London