Design, synthesis and anticonvulsant activities of novel 1-(substituted/unsubstituted benzylidene)-4-(4-(6,8-dibromo-2-(methyl/phenyl)-4- oxoquinazolin-3(4H)-yl)phenyl) semicarbazide derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 9, 2012, Pages 3072-3078

  Saravanan, Govindaraj ^a   Alagarsamy, Veerachamy ^b   Prakash, Chinnasamy Rajaram ^c  

^a BAPATLA COLLEGE OF PHARMACY   (India)

^b MNR College of Pharmacy   (India)

^c DCRM Pharmacy College   (India)

Author keywords

Epilepsy; In vivo studies; Neurotoxicity; Quinazolin 4(3H) one; Schiff base

Indexed keywords

1 (3 NITROBENZYLIDENE) 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (3 NITROBENZYLIDENE) 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 CHLOROBENZYLIDENE) 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 CHLOROBENZYLIDENE) 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 HYDROXY 3 METHOXYBENZYLIDENE) 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 HYDROXY 3 METHOXYBENZYLIDENE) 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 HYDROXYBENZYLIDENE) 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 HYDROXYBENZYLIDENE) 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 (4 NITROBENZYLIDENE) 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL]PHENYL)SEMICARBAZIDE; 1 (4 NITROBENZYLIDENE) 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 [4 (DIMETHYLAMINO)BENZYLIDENE] 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 [4 (DIMETHYLAMINO)BENZYLIDENE] 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 BENZYLIDENE 4 [4 (6,8 DIBROMO 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; 1 BENZYLIDENE 4 [4 (6,8 DIBROMO 4 OXO 2 PHENYLQUINAZOLIN 3(4H) YL)PHENYL]SEMICARBAZIDE; ANTICONVULSIVE AGENT; ETHOSUXIMIDE; PENTETRAZOLE; PHENYTOIN; QUINAZOLINONE DERIVATIVE; SEMICARBAZIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CLONIC SEIZURE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG PENETRATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRIC SHOCK; MOUSE; NEUROTOXICITY; NONHUMAN; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; ROTAROD TEST; SEIZURE THRESHOLD; SUBSTITUTION REACTION; TONIC CLONIC SEIZURE;

ANIMALS; ANTICONVULSANTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; NEUROTOXICITY SYNDROMES; QUINAZOLINONES; RATS; SEIZURES; SEMICARBAZIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 84859847666     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.03.068     Document Type: Article

References (34)

1. D.A. McCormick, and D. Contreras Annu. Rev. Physiol. 63 2001 815
2. R.S. Fisher, W. Emde Boas, W. Blume, C. Elger, P. Genton, P. Lee, and J. Engel Jr. Epilepsia 46 2005 470
3. J.O. McNamara Goodman & Gilman's the Pharmacologic Basis of Therapeutics 2001 McGraw-Hill New York 521
4. G. Kramer Epilepsia 42 2001 55
5. J.R. Pollard, and J. French Lancet Neurol. 1064 2006 5
6. P. Yogeeswari, D. Sriram, R. Thirumurugan, J.V. Raghavendran, K. Sudhan, R.K. Pavana, and J.P. Stables J. Med. Chem. 48 2005 6202
7. K.J. Meador J. Clin. Psychiatry 64 2003 30
8. Z. Lin, and P.K. Kadaba Med. Res. Rev. 17 1997 537
9. M.L. Wagner Am. J. Hosp. Pharm. 51 1994 1657
10. R.P. Shank, J.F. Gardocki, A.J. Streeter, and B.E. Maryanoff Epilepsia 41 2000 3
11. E.B. Nielsen, P.D. Suzdak, K.E. Andersen, L.J. Knutsen, U. Sonnewald, and C. Braestrup Eur. J. Pharmacol. 196 1991 257
12. R.H. Fuerst, N.M. Graves, I.E. Leppik, R.C. Brundage, G.B. Holmes, and R.P. Remmel Epilepsia 29 1988 488
13. M. Kubota, M. Nishi-Nagase, Y. Sakakihara, S. Noma, M. Nakamoto, H. Kawaguchi, and M. Yanagisawa Brain Dev. 22 2000 230
14. J.A. French Epilepsia 40 1999 s11
15. E. Perucca Br. J. Clin. Pharmacol. 42 1996 531
16. L. Bruno-Blanch, J. Galvez, and R. Garcia-Domenach Bioorg. Med. Chem. Lett. 13 2003 2749
17. E. Estrada, and A. Pena Bioorg. Med. Chem. 8 2000 2755
18. P. Kumar, B. Shrivastava, S.N. Pandeya, and J.P. Stables Eur. J. Med. Chem. 1006 2011 46
19. N.M. Abdel Gawad, H.H. Georgey, R.M. Youssef, and N.A. El-Sayed Eur. J. Med. Chem. 45 2010 6058
20. S.R. Pattan, V.V. KrishnaReddy, F.V. Manvi, B.G. Desai, and A.R. Bhat Indian J. Chem. 45B 2006 1778
21. M. Dinakaran, P. Selvam, E. Declercq, and S.K. Sridhar Biol. Pharm. Bull. 26 2003 1278
22. M.S. Mohamed, M.M. Kamel, E.M.M. Kassem, N. Abotaleb, S.L. Abd-El-moez, and M.F. Ahmed Eur. J. Med. Chem. 45 2010 3311
23. J.S. Shukla, and R. Shukla J. Indian Chem. Soc. 66 1989 209
24. V. Alagarsamy, V. Rajasolomon, R. Meena, and K.V. Ramseshu Biol. Pharm. Bull. 1091 2005 28
25. P. Panneerselvam, B.A. Rather, D.R.S. Reddy, and N.R. Kumar Eur. J. Med. Chem. 44 2009 2328
26. Y. Changwen, Y. Junhui, L. XiaoFeng, Y. Rong, W. Yabiao, L. Jun, and W. Yuliang Pestic. Biochem. Phys. 97 2010 194
27. S.S. Laddha, and S.P. Bhatnagar Bioorg. Med. Chem. 17 2009 6796
28. M. Wang, L.F. Wang, Y.Z. Li, Q.X. Li, Z.D. Xu, and D.M. Qu Trans. Met. Chem. 26 2001 307
29. L.A. Woodbury, and V.D. Davenport Arch. Int. Pharmacodyn. Ther. 92 1952 97
30. H.S. White, M. Johnson, H.H. Wolf, and H.J. Kupferberg Ital. J. Neurol. Sci. 16 1995 73
31. E.A. Swinyard, L.D. Clark, J.T. Miyahara, and H.H. Wolf J. Physiol. 132 1961 97
32. M.S. Dunham, and T.A. Miya J. Am. Pharm. Assoc. Sci. 46 1957 208
33. H. Rajak, R. Deshmukh, N. Aggarwal, S. Kashaw, M.D. Kharya, and P. Mishra Arch. Pharm. 342 2009 453
34. V. Alagarsamy, G. Muruganantham, and R. Venkateshaperumal Biol. Pharm. Bull. 26 2003 1711