Synthesis of N4-(2,4-dimethylphenyl) semicarbazones as 4-aminobutyrate aminotransferase inhibitors

Acta Pharmaceutica

Volumn 56, Issue 3, 2006, Pages 259-272

  Yogeeswari, Perumal ^a   Sriram, Dharmarajan ^a   Thirumurugan, Rathinasabapathy ^a   Jit, Logantha Ramamoorthy Jeewanlal Sunil ^a   Ragavendran, Jegadeesan Vaigunda ^a   Kavya, Ramkumar ^a   Rakhra, Kavya ^a   Saraswat, Vivek ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

2,4 dimethylphenyl semicarbazones; Anticonvulsants; GABA; GABA transaminase; Maximal electroshock; Pentylenetetrazole; Strychinine

Indexed keywords

4 AMINOBUTYRATE AMINOTRANSFERASE; 4 AMINOBUTYRATE AMINOTRANSFERASE INHIBITOR; 4 AMINOBUTYRIC ACID; CARBAMAZEPINE; N 4 (2,4 DIMETHYLPHENYL); PENTETRAZOLE; SEMICARBAZONE DERIVATIVE; STRYCHNINE; UNCLASSIFIED DRUG; UREA; ANTICONVULSIVE AGENT;

ANTICONVULSANT ACTIVITY; ARTICLE; BEHAVIOR; DEPRESSION; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRIC SHOCK; IN VITRO STUDY; NEUROTOXICITY; NONHUMAN; SEIZURE; SPECTROSCOPY; TREATMENT OUTCOME; ANIMAL; ANIMAL BEHAVIOR; BRAIN; DISEASE MODEL; DRUG ANTAGONISM; MALE; METABOLISM; MOUSE; RAT; SPRAGUE DAWLEY RAT; SYNTHESIS; WISTAR RAT;

4-AMINOBUTYRATE TRANSAMINASE; ANIMALS; ANTICONVULSANTS; BEHAVIOR, ANIMAL; BRAIN; DISEASE MODELS, ANIMAL; GAMMA-AMINOBUTYRIC ACID; MALE; MICE; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; SEIZURES; SEMICARBAZONES;

EID: 33748855540     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. K. J. Meador, Newer anticonvulsants: dosing strategies and cognition in treating patients with mood disorders and epilepsy, J. Clin. Psychiatry 64 (2003) 30-34.
2. G. A. B. Jones, Anticonvulsants, in Meyler's Side Effects of Drugs (Ed. M. N. G. Dukes), Elsevier Science Publishers B.V., New York 1988, pp. 120.
3. J. R. Dimmock, K. K. Sidhu, R. S. Thayer, P. Mack, M. J. Duffy, R. S. Reid and J. W. Quail, Anticonvulsant activities of some arylsemicarbazones displaying potent oral activity in the maximal electroshock screen in rats accompanied by high protection indices, J. Med. Chem. 36 (1993) 2243-2252.
4. J. R. Dimmock, R. N. Puthucode, J. M. Smith, M. Hetheriengton, J. W. Quail, U. Pugazhenthi, T. Lechler and J. P. Stables, (Aryloxy)aryl semicarbazones and related compounds: a novel class of anticonvulsant agents possessing high activity in the maximal electroshock screen, J. Med. Chem. 39 (1996) 3984-3987.
5. R. N. Puthucode, U. Pugazhenthi, J. W. Quail, J. P. Stables and J. R. Dimmock, Anticonvulsant activity of various aryl, arylidene and aryloxyaryl semicarbazones, Eur. J. Med. Chem. 33 (1998) 595-607.
6. J. R. Dimmock, S. C. Vashishtha and J. P. Stables, Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds, Eur. J. Med. Chem. 35 (2000) 241-248.
7. G. Heinisch, B. Matuszczak, D. Rakowitz and B. Tantisira, Synthesis of N-aryl-N′-heteroaryl-substituted urea and thiourea derivatives and evaluation of their anticonvulsant activity, Arch. Pharm. (Weinheim) 330 (1997) 207-210.
8. J. R. Dimmock, S. C. Vashishtha and J. P. Stables, Ureylene anticonvulsants and related compounds, Pharmazie 55 (2000) 490-494.
9. M. R. Pavia, S. J. Lobbestael, C. P. Taylor, F. M. Hershenson and D. L. Miskell, N-phenyl-N′-pyridinylureas as anticonvulsant agents, J. Med. Chem. 33 (1990) 854-861.
10. S. Moreau, P. Coudert, C. Rubat, D. Gardette, D. V. Goyet, J. Couquelet, P. Bastide and P. Tronche, Synthesis and anticonvulsant properties of new benzylpyridazine derivatives, J. Med. Chem. 37 (1994) 2153-2160.
11. V. Bailleux, L. Vallee, J. P. Nuyts and J. Vamecq, Anticonvulsant activity of some 4-amino-N-phenylphthalimides and N-(3-amino-2-methylphenyl) phthalimides, Biomed. Pharmacother. 48 (1994) 95-101.
12. S. N. Pandeya and J. R. Dimmock, Recent evaluations of thiosemicarbazones and semicarbazones and related compounds for antineoplastic and anticonvulsant activities, Pharmazie 48 (1993) 659-666.
13. P. Yogeeswari, R. Thirumurugan, R. Kavya, J. Selwyn Samuel and J. P. Stables, 2-Methyl, 3-chlorophenyl-substituted semicarbazones: Synthesis and anticonvulsant activity, Eur. J. Med. Chem. 39 (2004) 729-734.
14. S. G. Piredda, J. H. Woodhead and E. A. Swinyard, Effect of stimulus intensity on the profile of anticonvulsant activity of phenytoin, ethosuximide and valproate, J. Pharmacol. Exp. Ther. 232 (1985) 741-745.
15. W. Loscher, D. Honack, C. P. Fassbender and B. Nolting, The role of technical, biological and pharmacological factors in the laboratory evaluation of anticonvulsant drugs. III. Pentylenetetrazole seizure models, Epilepsy Res. 8 (1991) 171-189.
16. S. N. Pandeya, P. Yogeeswari and J. P. Stables, Synthesis and anticonvulsant activity of 4-bromophenyl substituted aryl semicarbazones, Eur. J. Med. Chem. 35 (2000) 879-886.
17. S. N. Pandeya, D. Sriram, P. Yogeeswari and J. P. Stables, Anticonvulsant and neurotoxicity evaluation of 5-(un)-substituted isatinimino derivatives, Pharmazie 56 (2001) 875-876.
18. P. Yogeeswari, D. Sriram, S. N. Pandeya and J. P. Stables, 4-Sulphamoylphenyl semicarbazones with anticonvulsant activity, Farmaco 59 (2004) 609-613.
19. P. Yogeeswari, D. Sriram, A. Brahmandam, I. Sridharan, R. Thirumurugan and J. P. Stables, Synthesis of novel aryl semicarbazones as anticonvulsants with GABA-mediated mechanism, Med. Chem. Res. 12 (2003) 57-68.
20. R. J. Porter, J. J. Cereghino, G. D. Gladding, B. J. Hessie, H. J. Kupferberg, B. Scotville and B. White, Antiepileptic drug development program, Cleveland Clin. Quart. 51 (1984) 293-305.
21. R. L. Krall, J. K. Penry, B. G. White, H. J. Kupferberg and E. A. Swinyard, Antiepileptic drug development: II. Anticonvulsant drug screening, Epilepsia 19 (1978) 409-428.
22. H. J. Kupferberg, Antiepileptic drug development program: a cooperative effort of government and industry, Epilepsia 30 (1989) S51-S56.
23. E. A. Swinyard, Experimental Models of Epilepsy, in A Manual for the Laboratory Worker (Eds. D. P. Purpura, J. K. Penry, D. M. Woodbury, D. B. Tower and R. D. Walter), Raven Press, New York 1972, pp. 210.
24. J. M. Brodie, Lamotrigine, Lancet 339 (1992) 1397-1399.
25. J. R. Boissier and P. Simon, Action of caffeine on the spontaneous motility of the mouse, Arch. Int. Pharmacodyn. Ther. 158 (1965) 212-220.
26. R. D. Porsolt, G. Anton, N. Blanet and M. Jalfre, Behavioural despair in rats: a new model sensitive to antidepressant treatments, Eur. J. Pharmacol. 47 (1978) 379-391.
27. C. F. Baxter and E. Roberts, Elevation of gamma-aminobutyric acid in rat brain with hydroxylamine, Proc. Soc. Exp. Biol Med. 101 (1959) 811-815.
28. E. Roberts, γ-Aminobutyric Acid, in Methods in Enzymology (Eds. S. P. Colowick and N. O. Kaplan), Vol. VI, Academic Press, New York 1962, p. 612.
29. E. N. Scott and W. B. Jakoby, Pyrrolidine metabolism: soluble gamma-aminobutyric transaminase and semialdehyde dehydrogenase, Science 128 (1958) 361-366.
30. B. Lippert, B. W. Metcalf, M. J. Jung and P. Casara, 4-amino-hex-5-enoic acid, a selective catalytic inhibitor of 4-aminobutyric-acid aminotransferase in mammalian brain, Eur. J. Biochem. 74 (1977) 441-445.
31. W. Loscher, C. P. Fassbender and B. Nolting, Epilepsy Res. 8 (1991) 79-94.
32. W. Zhang, K. F. Koehler, P. Zhang and J. M. Cook, Development of a comprehensive pharmacophore model for the benzodiazepine receptor, Drug Design Discov. 12 (1995) 193-248.