Synthesis of some novel 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone oxime ester derivatives and evaluation of their anticonvulsant activity

European Journal of Medicinal Chemistry

Volumn 57, Issue , 2012, Pages 275-282

  Karakurt, Arzu ^a   Alagöz, Mehmet A ^a   Sayoǧlu, Burcu ^b   Çalş, Ünsal ^b   Dalkara, Sevim ^b  

^a INONU UNIVERSITY   (Turkey)

^b HACETTEPE UNIVERSITY   (Turkey)

Author keywords

(arylalkyl)imidazole; Anticonvulsant activity; Azole derivatives; E Z isomers; Oxime ester

Indexed keywords

1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (2 CHLOROBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (2 METHOXYBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (2 METHYLBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (3 BROMOBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (3 CHLOROBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (3 METHOXYBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (3 METHYLBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (4 CHLOROBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (4 METHOXYBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (4 METHYLBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (4 NITROBENZOYL)OXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O (4 OXO 4 PHENYL)BUTANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O 2 METHYLBUT 2 ENOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O 2 PROPYLPENTANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O 3 METHYLBUTANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O 4 PHENYLBENZOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O BENZOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O BUTANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O CINNAMOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O CYCLOHEXANECARBONYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O HEXANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O PENTANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE O PROPANOYLOXIME; 1 (2 NAPHTHYL) 2 (IMIDAZOL 1 YL)ETHANONE OXIME ESTER DERIVATIVE; ANTICONVULSIVE AGENT; NAFIMIDONE; OXIME DERIVATIVE; PENTETRAZOLE; PHENYTOIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ELECTRIC SHOCK; EXPERIMENTAL MODEL; MOUSE; NEUROTOXICITY; NONHUMAN; SEIZURE; STRUCTURE ACTIVITY RELATION; TASK PERFORMANCE;

ANIMALS; ANTICONVULSANTS; ELECTROSHOCK; ESTERS; IMIDAZOLES; ISOMERISM; MICE; MOTOR ACTIVITY; NAPHAZOLINE; NEUROPSYCHOLOGICAL TESTS; OXIMES; SEIZURES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867433214     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.08.037     Document Type: Article

References (24)

1. S. Dalkara, and A. Karakurt Recent progress in anticonvulsant drug research: strategies for anticonvulsant drug development and applications of antiepileptic drugs for non-epileptic central nervous system disorders Curr. Top. Med. Chem. 2012
2. E. Perucca Marketed new antiepileptic drugs: are they better than old-generation agents? Ther. Drug Monit. 24 2002 74 80
3. J.S. Duncan The promise of new antiepileptic drugs Br. J. Clin. Pharmacol. 53 2002 123 131
4. J.C. Mulley, I.E. Scheffer, S. Petrou, and S.F. Berkovic Channelopathies as a genetic cause of epilepsy Curr. Opin. Neurol. 16 2003 171 176
5. H. Lerche, Y.G. Weber, K. Jurkat-Rott, and F. Lehmann-Horn Ion channel defects in idiopathic epilepsies Curr. Pharm. Des. 11 2005 2737 2752
6. M.J. Brodie Antiepileptic drug therapy the story so far Seizure Eur. J. Epilep. 19 2010 650 655
7. M.P. Jacobs, G.G. Leblanc, A. Brooks-Kayal, F.E. Jensen, D.H. Lowenstein, J.L. Noebels, D.D. Spencer, and J.W. Swann Curing epilepsy: progress and future directions Epilep. Behav. 14 2009 438 445
8. K.A. Walker, M.B. Wallach, and D.R. Hirschfeld 1-(naphthylalkyl)-1H- imidazole derivatives, a new class of anticonvulsant agents J. Med. Chem. 24 1981 67
9. D. Nardi, A. Tajana, A. Leonardi, R. Pennini, F. Portioli, M.J. Magistretti, and A. Subissi Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(omega-phenyl-omega-hydroxyalkyl)imidazoles J. Med. Chem. 24 1981 727
10. D.W. Robertson, J.H. Krushinski, E.E. Beedle, J.D. Leander, D.T. Wong, and R.C. Rathbun Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol J. Med. Chem. 29 1986 1577
11. D.W. Robertson, J.D. Leander, R. Lawson, E.E. Beedle, C.R. Clark, B.D. Potts, and C.J. Parli Discovery and anticonvulsant activity of the potent metabolic inhibitor 4-amino-N-(2,6-dimethylphenyl)-3,5-dimethylbenzamide J. Med. Chem. 30 1987 1742
12. G. Graziani, P. Cazzulani, C. Luca, G. Nava, and R. Testa Denzimol, a new anticonvulsant drug. II. General pharmacological activities Arzneimittel-Forsch 33 1983 1161 1168
13. U. Calis, S. Dalkara, M. Ertan, and R. Sunal The significance of the imidazole ring in anticonvulsant activity of (arylalkyl)imidazoles Arch. Pharm. (Weinheim) 321 1988 841
14. A. Karakurt, M. Ozalp, S. Isik, J.P. Stables, and S. Dalkara Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives Bioorg. Med. Chem. 18 2010 2902 2911
15. F. Ozkanli, S. Dalkara, U. Calis, and A. Willke Synthesis of some N-arylazole acetamide derivatives and their anticonvulsant and antimicrobial activities Arzneimittel-Forsch 44 1994 920 924
16. A. Karakurt, S. Dalkara, M. Ozalp, S. Ozbey, E. Kendi, and J.P. Stables Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities Eur. J. Med. Chem. 36 2001 421 433
17. W.G. Haney, R.G. Brown, E.I. Isaacson, and J.N. Delgado Synthesis and structure-activity relationships of selected isomeric oxime O-ethers as anticholinergic agents J. Pharm. Sci. 66 1977 1602 1606
18. A. Simay, L. Prokai, and N. Bodor Oxidation of aryloxyaminoalcohols with activated dimethylsulfoxide - a novel C-N oxidation facilitated by neighboring group effect Tetrahedron 45 1989 4091 4102
19. X.H. Liu, P. Cui, B.A. Song, P.S. Bhadury, H.L. Zhu, and S.F. Wang Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3- substituted-4,5-dihydropyrazol-1-yl)ethanone oxime ester derivatives Bioorg. Med. Chem. 16 2008 4075 4082
20. A. Balsamo, M.C. Breschi, G. Chielini, L. Favero, M. Macchia, A. Martinelli, C. Martini, A. Rossello, and R. Scatizzi Synthesis and beta-adrenergic properties of (E)-N-[3-(alkylamino)-2-hydroxypropylidene] (methyloxy) amines substituted with an aromatic group on their [(methyloxy)imino] methyl moiety (MOIMM) - an investigation into the biopharmacological effects of an aryl substitution in the class of MOIM beta-blocking drugs Eur. J. Med. Chem. 30 1995 743 755
21. A. Karakurt, M.D. Aytemir, J.P. Stables, M. Ozalp, F. Betul Kaynak, S. Ozbey, and S. Dalkara Synthesis of some oxime ether derivatives of 1-(2-naphthyl)-2-(1,2,4-triazol-1-yl)ethanone and their anticonvulsant and antimicrobial activities Arch. Pharm. (Weinheim) 339 2006 513 520
22. T. Immediata, and A.R. Day b-naphtyl derivatives of ethanolamine and N-substitüted ethanolamines J. Org. Chem. 5 1940 512 527
23. J.P. Stables, and H.J. Kupferberg The NIH Anticonvulsant Drug Development (ADD) Program: preclinical anticonvulsant screening project G.T.P. Avanzini, M. Avoli, Molecular and Cellular Targets for Antiepileptic Drugs 1997 John Libbey & Company Ltd. London 191 198
24. H.J. Kupferberg, and J.P. Stables Mechanism of action revisited: drug discovery testing and clinical prediction H.K.G. Stefan, B. Mamoli, Challenge Epilepsy - New Anticonvulsant Drugs 1998 Blackwell Science Ltd. Boston 7 29