Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

Medicinal Chemistry Research

Volumn 18, Issue 9, 2009, Pages 758-769

  Shafiee, Abbas ^a   Rineh, Ardeshir ^a   Kebriaeezadeh, Abbas ^a   Foroumadi, Alireza ^a,b   Sheibani, Vahid ^b   Afarinesh, Mohammad Reza ^b  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b KERMAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Anticonvulsant; Kindling model; Pentylenetetrazole; Semicarbazones

Indexed keywords

1 (1 (2 HYDROXYPHENYL)ETHYLIDENE) 4 (2 PHENOXYPHENYL)SEMICARBAZIDE; 1 (2,5 DIMETHOXYBENZYLIDENE) 4 (2 PHENOXYPHENYL)SEMICARBAZIDE; 1 (3 BROMOBENZYLIDENE 4 (2 PHENOXYPHENYL)SEMICARBAZIDE; 1 (4 (METHYLTHIO)BENZYLIDENE) 4 (2 PHENOXYPHENYL)SEMICARBAZIDE; 1 [1 [4 (METHYLTHIO)PHENYL]ETHYLIDENE]4 (2 PHENOXYPHENYL)SEMICARBAZIDE; 1 BENZYLIDENE 4 (2 PHENOXYLPHENYL)SEMICARBAZIDE; 4 (2 PHENOXYPHENYL) 1 ((PYRIDIN 2 YL)METHYLENE)SEMICARBAZIDE; 4 (2 PHENOXYPHENYL) 1 ((PYRIDIN 3 YL)METHYLENE)SEMICARBAZIDE; 4 (2 PHENOXYPHENYL) 1 ((PYRIDIN 4 YL)METHYLENE)SEMICARBAZIDE; 4 (2 PHENOXYPHENYL) 1 (1 4 TOLYLETHYLIDENE)SEMICARBAZIDE; 4 (2 PHENOXYPHENYL) 1 (1 PHENYLETHYLIDENE)SEMICARBAZIDE; ACETOPHENONE DERIVATIVE; ANTICONVULSIVE AGENT; BENZALDEHYDE DERIVATIVE; PENTETRAZOLE; SEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG; VALPROIC ACID;

ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CONVULSION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; KINDLING; MALE; MAXIMUM PERMISSIBLE DOSE; NEUROTOXICITY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

EID: 73449145107     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-009-9165-0     Document Type: Article

References (22)

1. A Almasirad N Vosooghi SA Tabatabai A Kebriaeezadeh A Shafiee 2007 Synthesis, anticonvulsant and muscle relaxant activities of substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1, 2, 4-triazole Acta Chim Slov 54 317 324 1:CAS:528:DC%2BD2sXot1OksrY%3D
2. A Costanzo G Guerrini G Ciciani F Bruni C Costagli S Selleri B Costa C Martini P Malmberg-Aiello 2003 Synthesis and pharmacological evaluation of 3-(2-furyl)- and 3-(3-furyl)-8-chloropyrazolo[5, 1-c][1, 2, 4]benzotriazine 5-oxides, new 3-heteroaryl substituted benzodiazepine receptor ligands Med Chem Res 11 87 101
3. P Czapinski B Blaszccczyk SJ Czuczwar 2005 Mechanism of action of antiepileptic drugs Curr Top Med Chem 5 3 14 10.2174/1568026053386962 10.2174/1568026053386962 1:CAS:528:DC%2BD2MXpsFOgsg%3D%3D 15638774 (Pubitemid 40202106)
4. S Emami A Kebriaeezadeh MJ Zamani A Shafiee 2006 Azolylchromans as a novel scaffold for anticonvulsant activity Bioorg Med Chem Lett 16 1803 1806 10.1016/j.bmcl.2006.01.004 10.1016/j.bmcl.2006.01.004 1:CAS:528: DC%2BD28XhvVyrtLY%3D 16439117 (Pubitemid 43267354)
5. RS Fisher 1989 Animal models of the epilepsies Brain Res Brain Res Rev 14 245 278 10.1016/0165-0173(89)90003-9 10.1016/0165-0173(89)90003-9 1:CAS:528:DyaK3cXlsVCj 2679941 (Pubitemid 19247337)
6. A Foroumadi V Sheibani A Sakhteman M Rameshk M Abbasi R Farazifard SA Tabatabai A Shafiee 2007 Synthesis and anticonvulsant activity of novel 2-amino-5-[4-chloro-2-(2-chlorophenoxy) phenyl]-1,3,4thiadiazole derivatives Daru J Fac Pharm 15 89 93 1:CAS:528:DC%2BD2sXhtV2rur7N
7. GV Goddard DC Mcintyre CH Leech 1969 A permanent change in brain function resulting from daily electricl stimulation Exp Neurol 25 295 330 10.1016/0014-4886(69)90128-9 10.1016/0014-4886(69)90128-9 1:STN:280: DyaE3c%2FjtlOjsw%3D%3D 4981856
8. SGA Hamid HA El-Obeid AA Al-Majed HA El-Kashef HI El-Subbagh 2001 Synthesis and anticonvulsant activity of some new 4-oxo-3H-quinazoline analogs Med Chem Res 10 378 389
9. A Kebriaeezadeh S Emami M Ebrahimi M Sharifazdeh R Khorasani A Shafiee 2008 Anticonvulsant and antiepileptogenic effects of azolylchromanones on lithium-pilocarpine induced seizures and pentylenetetrazole-kindling model of epilespy Biomed Pharmacother 62 208 211 10.1016/j.biopha.2007.12.003 10.1016/j.biopha.2007.12.003 1:CAS:528:DC%2BD1cXls1Sisb4%3D 18222059 (Pubitemid 351626444)
10. H Kupferberg 2001 Animal models used in the screening of antiepileptic drugs Epilepsia 42 7 12 11564118
11. RL Macdonald KM Kelly 1995 Antiepileptic drug mechanisms of action Epilepsia 36 S2 S12 10.1111/j.1528-1157.1995.tb05996.x 10.1111/j.1528-1157.1995. tb05996.x 1:CAS:528:DyaK2MXmslymtbo%3D 8784210
12. B Malawska 2005 New anticonvulsant agents Curr Top Med Chem 5 69 85 10.2174/1568026053386944 10.2174/1568026053386944 1:CAS:528: DC%2BD2MXpsFOgtw%3D%3D 15638779 (Pubitemid 40202111)
13. HH Meritt TJ Putnam 1937 Experimental determination of the anticonvulsant properties of some phenyl derivatives Science 85 525 526 10.1126/science.85. 2213.525 10.1126/science.85.2213.525
14. Meritt HH, Putnam TJ (1938) Sodium diphenyl-hydantoinate in the treatment of convulsive disorders. J Am Med Assoc 111:106S
15. SN Pandeya H Manjula JP Stables 2001 Design of semicarbazones and their bioisosteric analogues as potential anticonvulsants Pharmazie 56 121 124 1:CAS:528:DC%2BD3MXht1KktLo%3D 11234338
16. A Rineh N Mahmoodi M Abdollahi A Foroumadi M Sorkhi A Shafiee 2007 The synthesis, analgesic and anti-inflammatory activities of 4-(2-phenoxyphenyl) semicarbazones Arch Pharm (Weinheim) 340 409 415 10.1002/ardp.200700045 10.1002/ardp.200700045 1:CAS:528:DC%2BD2sXpslCgsLo%3D (Pubitemid 47291184)
17. A Samzadeh-Kermani H Shafaroodi R Miri H Mirkhani M Vosooghi A Shafiee 2009 Synthesis, calcium channel antagonist activity and protection against pentyleneterazole-induced seizure Med Chem Res 18 112 126 10.1007/s00044-008- 9112-5 1:CAS:528:DC%2BD1MXhtVWlsbk%3D
18. JW Sanders 1993 Some aspects of prognosis in the epilepsies. A review Epilepsia 34 1007 1016 10.1111/j.1528-1157.1993.tb02126.x 10.1111/j.1528-1157. 1993.tb02126.x (Pubitemid 24004236)
19. P Yogeeswari D Sriram A Brahmandam I Sridharan R Thirumurugan JP Stables 2003 Synthesis of novel aryl semicarbazones as anticonvulsants with GABA-mediated mechanism Med Chem Res 12 57 68 1:CAS:528:DC%2BD3sXovVKitr0%3D
20. P Yogeeswari D Sriram R Thirumurugan JV Raghavendran K Sudhan RK Pavana J Stables 2005 Discovery of N-(2,6-dimethylphenyl)-substituted semicarbazones as anticonvulsants effective against various animal models of seizure with GABA-T inhibitory activity J Med Chem 48 6202 6211 10.1021/jm050283b 10.1021/jm050283b 1:CAS:528:DC%2BD2MXpvFSnu7k%3D 16190747 (Pubitemid 41428975)
21. P Yogeeswari D Sriram V Veena R Kavya K Rakhra J Vaigunda Ragavendran S Mehta R Thirumurugan JP Stables 2005 Synthesis of aryl semicarbazones as potential anticonvulsant agents Biomed Pharmacother 59 51 55 10.1016/j.biopha.2004.04.013 10.1016/j.biopha.2004.04.013 1:CAS:528: DC%2BD2MXhvVSgsLw%3D 15740936 (Pubitemid 40312280)
22. A Zarghi SA Tabatabai M Faizi A Ahadian P Navabi V Zanganeh A Shafiee 2005 Synthesis and anticonvulsant activity of new 2-substituted-5-(2- benzyloxyphenyl)-1,3,4-oxadiazoles Bioorg Med Chem Lett 15 1863 1865 10.1016/j.bmcl.2005.02.014 10.1016/j.bmcl.2005.02.014 1:CAS:528: DC%2BD2MXisVCntb4%3D 15780622 (Pubitemid 40380748)