Characterization of the anticonvulsant profile of valpromide derivatives

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 14, 2004, Pages 3857-3869

  Tasso, Silvina M ^a   Moon, Sung Ch ^a   Bruno Blanch, Luis E ^a   Estiú, Guillermina L ^b  

^a FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Anticonvulsant activity; Antiepileptic drugs; Pharmacophore; Valpromide derivatives

Indexed keywords

BATRACHOTOXININ A 20ALPHA BENZOATE; SODIUM; SODIUM CHANNEL; VALPROIC ACID DERIVATIVE; VALPROMIDE; VOLTAGE GATED SODIUM CHANNEL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DRUG BINDING; DRUG COMPETITION; DRUG STRUCTURE; MOUSE; NONHUMAN; PHARMACOPHORE; SEIZURE SUSCEPTIBILITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTICONVULSANTS; DRUG EVALUATION, PRECLINICAL; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED BALB C; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; VALPROIC ACID;

EID: 2942701907     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.05.003     Document Type: Article

References (83)

1. Rogawski M., Porter R. Pharmacol. Rev. 49(3):1990;122
2. Loscher W., Schmidt D. Epilepsy Res. 17:1994;95
3. Bialer M., Johannessen S.I., Kupferberg H.K., Levy R.H., Loiseau P., Perucca E. Epilepsy Res. 25:1996;299
4. Bialer M., Johannessen S.I., Kupferberg H.K., Levy R.H., Loiseau P., Perucca E. Epilepsy Res. 51:2002;31
5. Bialer M., Johannessen S.I., Kupferberg H.K., Levy R.H., Loiseau P., Perucca E. Epilepsy Res. 43:2001;11
6. Anger T., Madge D., Mulla M., Riddall D. J. Med. Chem. 44:2001;115
7. Moldrich R.X., Beart P.M., Jane D.E., Chapman A.G., Meldrum B.S. Neuropharmacology. 40:2001;732
8. Vamecq J., Bac P., Herrenknecht C., Maurois P., Delcourt P., Stables J. J. Med. Chem. 43:2000;1311
9. Loscher W., Leppik I.E. Epilepsy Res. 50:2002;17
10. Jain K.K. Exp. Opin. Invest. Drugs. 9(4):2000;1
11. Pevarello P., Bonsignori A., Caccia C., Amici R., McArthur R., Fariello R., Salvati P., Varasi M. Bioorg. Med. Chem. Lett. 9:1999;2521
12. Villetti G., Bregola G., Bassani F., Bergamaschi M., Rondelli I., Pietra C., Simonato M. Neuropharmacology. 40:2001;866
13. Andurkar S., Beguin C., Stables J., Kohn H. J. Med. Chem. 2001;44
14. Grimm J.B., Stables J.P., Milton L.B. Bioorg. Med. Chem. 11:2003;4133
15. Treiman D.M. Epilepsia. 42(Suppl. 3):2001;8
16. Brodie M.J., Dichter M.A. N. Engl. J. Med. Chem. 334:1996;1583
17. White H.S. Epilepsia. 40(Suppl. 5):1999;S2
18. White H.S. Epilepsia. 44(Suppl. 7):2003;2
19. Ragsdale D.S., Avoli M. Brain Res. Rev. 26:1998;16
20. Pugsley M.K., Yu E.J., McLean T.H., Goldin A.L. Proc. West. Pharmacol. Soc. 42:1999;105
21. Netzeva T., Doytchinova I., Natcheva R. Pharm. Res. 17(6):2000;727
22. Unverferth K., Engel J., Hofgen N., Rostock A., Gunther R., Lankau H., Menzer M., Rolfs A., Liebscher J., Muller B., Hofmann H. J. Med. Chem. 41:1998;63
23. Malawska B., Kulig K., S'Piewaka A., Stables J. Bioorg. Med. Chem. 12:2004;625
24. Pandeya S.N., Raja A.S. J. Pharm. Sci. 2002;266
25. Cox, B.; Nobbs, M. S.; Shah, G. P.; Edney, D. D.; Loft, M. S. Patent WO9838174, 1998
26. Tasso S.M., Bruno-Blanch L.E., Estiu G.L. J. Mol. Model. 7:2001;231
27. Brown M.L., Zha C.C., Van Dyke C.C., Brown G.B., Brouillette W.J. J. Med. Chem. 42:1999;1537
28. Cox, B.; Healy, M. P.; Nobbs, M. S.; Shah, G. P. Patent WO9932462, 1999
29. Salvati P., Maj R., Caccia C., Cervini M.A., Fornaretto M., Lamberti E., Pevarello P., Skeen G.A., White H.S., Wolf H.H., Faravelli L., Mazzanti M., Mancinelli E., Varasi M., Fariello R. J. Pharmacol. Exp. Ther. 288:1999;1151
30. Fariello R., McArthur R.A., Bonsignori A., Cervini M.A., Maj R., Pevarello P., Wolf H.H., Woodhead J.W., White H.S., Varasi M., Salvati P., Post C. J. Pharmacol. Exp. Ther. 285:1998;397
31. Reddy P.A., Hsiang B.C., Latifi T.N., Hill M.W., Woodward K.E., Rothman S.M., Ferendelli J.A., Covey D.F. J. Med. Chem. 39:1996;1898
32. Hill M.W., Reddy P.A., Covey D.F., Rothman S.M. J. Pharmacol. Exp. Ther. 285:1998;1303
33. Rundfelt C. Epilepsy Res. 34:1999;57
34. Ferrendelli, J. A.; Holland, K. D. In Antiepileptic Drugs, 3rd ed.; Levy, R., Mattson, R., Meldrum, B., Penry, J. K., Dreifuss, F. E., Eds.; Raven: New York, 1989; Vol. 1.
35. Fisher R.S. Brain Res. Rev. 14:1989;245
36. Benes J., Parada A., Figueirredo A.A., Alves P.C., Freitas A.P., Learmmonth D.A., Cunha R.A., Garrett J., Soares-da-Silva P. J. Med. Chem. 42:1999;2582
37. Taylor C.P., Meldrum B.S. TiPS. 16:1995;309
38. Vamecq J., Lambert D., Poupaert J., Masereel B., Stables J.P. J. Med. Chem. 41:1998;3307
39. Maillard M.C., Perlman M.E., Amitay O., Baxter D., Berlove D., Connaughton S., Fischer J.B., Guo J., Hu L., McBurney R.N., Nagy P.I., Subbarao K., Yost E.A., Zhang L., Durant G.J. J. Med. Chem. 41:1998;3048
40. Fischer W., Bodewel R., Satzinger G. Arch. Pharmacol. 346:1992;442
41. Molnár P., Erdo S.L. Eur. J. Pharmacol. 273:1995;303
42. QSAR Properties Versión 7.00. HyperChem Release 7.01 for Windows Molecular Modeling System 2002. Hypecube Inc. 1115 NW 4th Street, Gainesville, Florida 32601, USA
43. Willow M., Catterall W.A. Mol. Pharmacol. 22:1982;627
44. Willow M., Kuenzel E.A., Catterall W.A. Mol. Pharmacol. 25:1984;228
45. Chen A., Weston J.K., Bratton A.C. Epilepsia. 4:1963;66
46. SYBYL is a product Tripos, Inc., San Diego CA
47. Loscher W., Nau H. Neuropharmacology. 24(5):1985;427
48. Abbott F.S., Acheampong A.A. Neuropharmacology. 27(3):1988;287
49. Elmazar M.M., Hauck R.S., Nau H. J. Pharm. Sci. 82(12):1993;1255
50. Perucca E. CNS Drugs. 16(10):2002;695
51. Hadad S., Vree T., Van der Kleijn E., Bialer M. J. Pharm. Sci. 81:1992;1047
52. Rekatas G.V., Tani E., Demopoulos V., Kourounakis P. Arch. Pharm. Pharm. Med. Chem. 329:1996;393
53. Levi M., Yagen B., Bialer M. Pharm. Res. 14(2):1997;213
54. Keane P.E., Simiand J., Mendes E., Santucci V. Neuropharmacology. 22:1983;875
55. Loscher W., Nau H. Neuropharmacology. 24:1985;427.41
56. Abbott F.S., Acheampong A.A. Neuropharmacology. 27:1988;287
57. Bialer M., Hadad S., Kadry B., Abdul-Hai A., Haj-Yehia A., Sterling J., Herzig Y., Yagen B. Pharm. Res. 13:1996;284
58. Bialer M. Clin. Pharmacokinet. 20:1991;114
59. Haj-Yehia A., Bialer M. Pharm. Res. 6:1989;682
60. Haj-Yehia A., Hadad S., Bialer M. Pharm. Res. 9:1992;1058
61. Bialer M., Kadry B., Abdul-Hai A., Haj-Yehia A., Sterling J., Herzig Y., Shirvan M. Biopharm. Drug Dispos. 17:1996;565
62. Hadad S., Bialer M. Pharm. Res. 12:1995;905
63. Spiegelstein O., Kroetz D.L., Levy R.H., Yagen B., Hurst S.I., Levi M., Haj-Yehia A., Bialer M. Pharm. Res. 17:2000;216
64. Porter M., Cereghino M., Gladding R., Hessie B., Kupferberg D., Scoville M., White D. Clev. Clin. Q. 51:1984;293
65. Edafiogho, I.; Scott, K. In Burgera's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M., Ed.; John Wiley and Sons, 1996.
66. Gladding, G. D.; Kupferberg, H. J.; Swinyard, E. A. In Handbook Exp. Pharm. 1985; Vol. 74, pp 341-347
67. Swinyard E.A., Woodhead J.H., White H.S., Franklin M.R. Levy R., Mattson R., Meldrum B., Penry J.K., Dreifuss F.E. Antiepileptic Drugs. 3rd ed. 1989;85-102 Raven, New York
68. Scriba G.K.E. Arch. Pharm. Pharm. Med. Chem. 329:1996;554
69. Tantisira B., Tantisira M.H., Patarapanich C., Sooksawate T., Chunngam T. Res. Commun. Mol. Pathol. Pharmacol. 97:1997;151
70. Bialer, M.; Haj-Yehia, A.; Badir, K.; Hadad, S. Pharmacy World & Science 1994, 16, 2
71. Masereel B., Rolin S., Abbate F., Scozzafava A., Supuran C. J. Med. Chem. 45(2):2002;312
72. Chufán E.E., Pedregosa J.C., Baldini O.N., Bruno-Blanch L. Il Fármaco. 54:1999;838
73. Tasso S., Bruno-Blanch L., Moon S.Ch., Estiu G. J. Mol. Struct. (THEOCHEM). 504:2000;229
74. Maryanoff B., Costanzo M., Nortey S., Greco M., Shank R., Schupsky J., Ortegon M., Vaught J. J. Med. Chem. 41:1998;1315
75. Litchfield J.T., Wilcoxon F. J. Pharmacol. Exp. Ther. 96:1949;99
76. Trainer V.L., Moreau E. J. Biol. Chem. 268(23):1993;17114
77. Creveling C.R. Mol. Pharmacol. 23:1983;350
78. Frisch M. J.; Trucks, G. W.; Schlegel, H. B; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, C.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98; Gaussian: Pittsburgh PA; 1998
79. Becke A.D. J. Chem. Phys. 98:1993;5648
80. Lee C., Yang W., Parr R.G. Phys. Rev. B. B37:1988;785
81. Breneman C.N., Wiberg K.B. J. Comp. Chem. 11:1990;361
82. Breneman C.N., Wiberg K.B. Science. 16:1994;2
83. Greenwal R.B., Zhao H., Yang K., Reddy P., Martinez A. J. Med. Chem. 47:2004;726