Impact of aromatic substitution on the anticonvulsant activity of new N-(4-arylpiperazin-1-yl)-alkyl-2-azaspiro[4.5]decane-1,3-dione derivatives

Pharmacological Reports

Volumn 58, Issue 2, 2006, Pages 207-214

  Obniska, Jolanta ^a   Kamiński, Krzysztof ^a   Tatarczyńska, Ewa ^b  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^b INSTITUTE OF PHARMACOLOGY   (Poland)

Author keywords

2 azaspiro 4.5 decane 1,3 diones; Anticonvulsant activity; Pyrrolidine 2,5 diones; Spirosuccinimides

Indexed keywords

ANTICONVULSIVE AGENT; CYCLOHEXANE; N (4 ARYLPIPERAZIN 1 YL)ALKYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE DERIVATIVE; N [2 (4 PHENYLPIPERAZIN 1 YL)ETHYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 (4 PHENYLPIPERAZIN 1 YL)ETHYL][7,8 F]BENZO 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]ETHYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]ETHYL][7,8 F]BENZO 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]ETHYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]ETHYL][7,8 F]BENZO 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 [4 (3 TRIFLUOROMETHYLPHENYL)PIPERAZIN 1 YL]ETHYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [2 [4 (3 TRIFLUOROMETHYLPHENYL)PIPERAZIN 1 YL]ETHYL][7,8 F]BENZO 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL][7,8 F]BENZO 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [3 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]PROPYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [3 [4 (3 TRIFLUOROMETHYLPHENYL)PIPERAZIN 1 YL]PROPYL] 8 PHENYL 2 AZASPIRO[4.5]DECANE 1,3 DIONE; N [3 [4 (3 TRIFLUOROMETHYLPHENYL)PIPERAZIN 1 YL]PROPYL][7,8 F]BENZO 2 AZASPIRO[4.5]DECANE 1,3 DIONE; PHENYTOIN; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG; VALPROATE MAGNESIUM;

ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG SCREENING; DRUG SYNTHESIS; ELECTRIC SHOCK; MALE; MOUSE; NEUROTOXICITY; NONHUMAN;

EID: 33646763206     PISSN: 22995684     EISSN: 22995684     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

1. Alexander MS, Stables JP, Ciechanowicz-Rutkowska M, Hursthouse M, Hibbs D, Edafiogho IO, Moore VA, Scott KR: Spirane 6. Ring A homologues N-benzyloxy-2-azaspiro [4.4]nonane-1,3-dione. Eur J Med Chem, 1996, 31, 787-795.
2. 2 receptor affinity of some 2- and 3-substituted 1,2,3,4-tetrahydro-β-carbolines. Pharmazie, 1993, 48, 289-294.
3. Edafiogho IO, Scott KR, Moore JA, Farrar VA, Nicholson JM: Synthesis and anticonvulsant activity of imidooxy derivatives. J Med Chem, 1991, 34, 387-392.
4. Faust JA, Jules LH, Yee L: Anticonvulsants: Spirohydantoines and derivatives of tetrahydronaphthalene. J Am Pharm Assoc, 1957, 40, 21-26.
5. Heinecke K, Thiel W: Identity and physicochemical properties of 1-(4-chlorophenyl)-4-morpholinoimidazolin-2-one, AWD 131-138. Pharmazie, 2001, 56, 458-461.
6. Joshi H, Upadhyay P, Karia D, Baxi AJ: Synthesis of some novel imidazolinones as potent anticonvulsant agents. Eur J Med Chem, 2003, 38, 837-840.
7. Krall RL, Penry JK, White BG, Kupferberg HJ, Swinyar EA: Antiepileptic drug development II. Anticonvulsant drug screening. Epilepsia, 1978, 19, 400-428.
8. Kupferberg HJ: Antiepileptic drug development program: A cooperative effort of government and industry. Epilepsia, 1989, 30, Suppl, 51-56.
9. Litchfield LT, Wilcoxon F: A simplified method of evaluating dose effect experiments. J Pharmacol Exp Ther, 1949, 96, 99-113.
10. Obniska J, Jurczyk S, Zejc A, Kamiński K, Tatarczyńska E, Stachowicz K: Anticonvulsant properties of N-(4-methylpiperazin-1-yl) and N-[(4-methylpiperazin-1 yl)-propyl] derivatives of 3-aryl and 3-spirocycloalkylpyrrolidine-2,5-dione. Pharmacol Rep, 2005, 57, 170-175.
11. Obniska J, Kulig K, Zejc A: Synthesis and anticonvulsant properties of new N-piperazinylalkyl imides of succinic acid. Acta Pol Pharm - Drug Res, 1998, 55, 223-231.
12. 2A receptor activity of new N-[3-(4-phenylpiperazin-1-yl)-propyl] derivatives of 3-spito-cyclohexanepyrrolidine-2,5-dione and 3-spiro-β-tetralonepyrrolidine-2,5-dione. Pol J Pharmacol, 2003, 55, 553-557.
13. Obniska J, Zagórska A: Synthesis and anticonvulsant properties of new N-[4-arylpiperazin-1-yl)-methyl] derivatives of 3-aryl pyrrolidine-2,5-dione and 2-azaspiro [4,4]nonane-1,3-dione. Il Farmaco, 2003, 58, 1227-1234.
14. Obniska J, Zejc A, Karolak-Wojciechowska J: Synthesis, physicochemical and anticonvulsant properties of new N-pyridyl derivatives of 3-phenyl- and 3,3-diphenylsuccinimides. Il Farmaco, 1999, 54, 423-429.
15. Obniska J, Zejc A, Zagórska A: Synthesis and anticonvulsant properties of new 1-phenyl and 1-phenylamino-3-phenylpyrrolidine-2,5-dione derivatives. Acta Pol Pharm - Drug Res, 2002, 59, 209-213.
16. Schenck HA, Lenkowski PW, Choudhury-Mukherjee I, Seon-Hoon Ko, Stables JP, Patel MK Brown ML: Design, synthesis and evolution of novel hydroxyamides as orally available anticonvulsants. Bioorg Med Chem, 2004, 12, 979-993.
17. Scott KR, Edafiogho IO, Moore JA, Nicholson JM: Synthesis and anticonvulsant activity of a spirosuccinimide. Pharmacy World J, 1991, 8, 44-50.
18. Scott KR, Moore JA, Zalusky TB, Edafiogho IO, Moore JA, Nicholson JM, Lee M, Hinko ChN: Cyclic analogues of valproic acid. Synthesis and anticonvulsant activity. J Med Chem, 1985, 28, 413-417.
19. Smart BE: Fluorine substituent effects (on bioactivity). J Fluorine Chem, 2001, 109, 3-11.
20. Swinyard BA, Brown WC, Goodman LS: Comparative assays of antiepileptic drugs in mice and rats. J Pharmacol Exp Ther, 1952, 106, 319-330.
21. Tarver ML, Nicholson JM, Scott KR: Spirosuccinimides as potential anticonvulsants. J Pharm Sci, 1985, 74, 785-787.
22. Unverfert K, Engel J, Hofgen N, Rostock A, Gunter R, Lankau FU, Menzer M, Rolfs A et al.: Synthesis, anticonvulsant activity, and structure-activity relationships of sodium channel bloking 3-aminopyrroles. J Med Chem, 1998, 41, 63-73.
23. Wong MG, Defina JA, Andrews PR: Conformational. analysis of clinically active anticonvulsant drugs. J Med Chem, 1986, 29, 562-572.
24. 4-phtalimido phenyl (thio) semicarbazides. Eur J Pharm Sci, 2003, 20, 341-349.