Design, synthesis and evaluation of anticonvulsant activity of pyridinyl-pyrrolidones: A pharmacophore hybrid approach

Archiv der Pharmazie

Volumn 345, Issue 3, 2012, Pages 185-194

  Siddiqui, Nadeem ^a   Ahsan, Waquar ^a   Alam, M Shamsher ^a   Ali, Ruhi ^a   Srivastava, Kamna ^b  

^a HAMDARD UNIVERSITY   (India)

^b UNIVERSITY OF DELHI   (India)

Author keywords

Anticonvulsants; Pharmacophore; Pyridinyl; Pyrrolidones; Synthesis

Indexed keywords

1 (3 CYANO 4,6 DIPHENYL PYRIDIN 2 YL) 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 (3 CYANO 6 PHENYL 4 (4 METHYLPHENYL)PYRIDIN 2 YL) 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [3 CYANO 4 (2 HYDROXYPHENYL) 6 (4 NITROPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [3 CYANO 4 (2 HYDROXYPHENYL) 6 PHENYL PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [3 CYANO 4 (4 HYDROXYPHENYL) 6 (4 NITROPHENYL) PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [3 CYANO 4 (4 HYDROXYPHENYL) 6 PHENYL PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [3 CYANO 6 (4 NITROPHENYL) 4 (4 METHYLPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [3 CYANO 6 (4 NITROPHENYL) 4 PHENYL PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [4 (4 CHLOROPHENYL) 3 CYANO 6 (4 NITROPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [4 (4 CHLOROPHENYL) 3 CYANO 6 PHENYL PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [4,6 BIS(4 CHLOROPHENYL) 3 CYANO PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 BROMOPHENYL) 3 CYANO 4 (2 HYDROXYPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 BROMOPHENYL) 3 CYANO 4 (4 HYDROXYPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 BROMOPHENYL) 3 CYANO 4 (4 METHYLPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 BROMOPHENYL) 3 CYANO 4 PHENYL PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 BROMOPHENYL) 4 (4 CHLOROPHENYL) 3 CYANO PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 CHLOROPHENYL) 3 CYANO 4 (2 HYDROXYPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 CHLOROPHENYL) 3 CYANO 4 (4 HYDROXYPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 CHLOROPHENYL) 3 CYANO 4 (4 METHYLPHENYL)PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; 1 [6 (4 CHLOROPHENYL) 3 CYANO 4 PHENYL PYRIDIN 2 YL] 5 OXOPYRROLIDINE 3 CARBOXYLIC ACID; ALANINE AMINOTRANSFERASE; ANTICONVULSIVE AGENT; ASPARTATE AMINOTRANSFERASE; CARBAMAZEPINE; CENTRAL DEPRESSANT AGENT; PHENOBARBITAL; PHENYTOIN; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ARTICLE; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VIVO STUDY; LIVER TOXICITY; MOTOR DYSFUNCTION; MOUSE; NEUROTOXICITY; NONHUMAN; PHARMACOPHORE; PHASE 1 CLINICAL TRIAL; PHASE 2 CLINICAL TRIAL; PRIORITY JOURNAL;

ANIMALS; ANTICONVULSANTS; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTROSHOCK; FEMALE; LIVER; MALE; MICE; PENTYLENETETRAZOLE; PYRIDINES; PYRROLIDINONES; SEIZURES; STRUCTURE-ACTIVITY RELATIONSHIP; TOXICITY TESTS;

EID: 84858066248     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201100140     Document Type: Article

References (21)

1. M. G. Wong, J. A. Defina, P. R. Andrews, J. Med. Chem. 1986, 29, 562-572.
2. A. Camerman, N. Camerman, In:, G. H. Glaser, J. K. Penry, D. M. Woodbury, eds. Antiepileptic Drugs: Mechanisms of Action, Raven Press, New York 1980, pp. 223-231.
3. S. M. Tasso, L. E. Bruno-Blanch, S. C. Moon, G. L. Estiu, J. Mol. Struct. 2000, 504, 229-240.
4. M. J. Kornet, J. Het. Chem. 1985, 22, 129-130.
5. H. Sasaki, Y. Mori, J. Nakamura, J. Shibasaki, J. Med. Chem. 1991, 34, 628-633.
6. K. Kaminski, J. Obniska, Bioorg. Med. Chem. 2008, 16, 4921-4931.
7. P. L. Canonico, E. Aronica, V. Bruno, M. V. Catania, G. Aleppo, F. Galavotti, F. Nicoletti, Funct. Neurol. 1990, 5, 121-126.
8. B. M. Kenda, A. C. Matagne, P. E. Talaga, P. M. Pasau, E. Differding, B. I. Lallemand, A. M. Frycia, F. G. Moureau, H. V. Klitgaard, M. R. Gillard, B. Fuks, P. Michel, J. Med. Chem. 2004, 47, 530-549.
9. J. M. Chezal, J. Paeshuyse, V. Gaumet, D. Canitrot, A. Maisonial, C. Lartigue, A. Gueiffier, E. Moreau, J. C. Teulade, O. Chavignon, J. Neyts, Eur. J. Med. Chem. 2010, 45, 2044-2047.
10. K. K. Borowicz, J. J. Luszczki, S. J. Czuczwar, Pharmacol. Rep. 2009, 61, 621-630.
11. B. B. Subudhi, P. K. Panda, S. P. Swain, P. Sarangi, Acta. Pol. Pharm. 2009, 66, 147-153.
12. T. C. Kang, J. H. Kang, H. T. Kim, S. J. Lee, U. K. Choi, J. E. Kim, S. E. Kwak, D. W. Kim, S. Y. Choi, O. S. Kwon, Neuropharmacol. 2008, 54, 954-964.
13. K. Kaminski, J. Obniska, Acta. Pol. Pharm-Drug Res. 2008, 65, 457-465.
14. R. L. Krall, J. K. Penry, B. G. White, H. J. Kupferberg, E. A. Swinyard, Epilepsia 1978, 19, 409-428.
15. C. R. Clark, M. J. M. Wells, R. T. Sansom, G. N. Norris, R. C. Dockens, W. R. Ravis, J. Med. Chem. 1984, 27, 779-782.
16. J. T. Litchfield, F. Wilcoxon, J. Pharmacol. Exp. Ther. 1949, 96, 99-113.
17. N. W. Dunham, T. A. Miya, J. Am. Pharm. Assoc. Sci. 1957, 46, 208-209.
18. S. Reitman, S. A. Frankel, Am. J. Clin. Pathol. 1957, 28, 56-63.
19. E. J. King, A. R. Armstrong, Can. Med. Assoc. J. 1934, 31, 376-381.
20. B. R. Brooks, R. E. Bruccoleri, B. D. Olafson, D. J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 1983, 4, 187-217.
21. N. D. Eddington, D. S. Cox, R. R. Roberts, R. J. Butcher, I. O. Edafiogho, J. P. Stables, N. Cooke, A. M. Goodwin, C. A. Smith, K. R. Scott, Eur. J. Med. Chem. 2002, 37, 635-648.