Functionalized amido ketones: New anticonvulsant agents

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 19, 2003, Pages 4275-4285

  Béguin, Cécile ^a   Andurkar, Shridhar V ^a,b   Jin, Albert Y ^c   Stables, James P ^d   Weaver, Donald F ^e   Kohn, Harold ^f  

^a University of Houston   (United States)

^b MIDWESTERN UNIVERSITY   (United States)

^c QUEEN S UNIVERSITY   (Canada)

^d NATIONAL INSTITUTE OF NEUROLOGICAL DISORDERS AND STROKE   (United States)

^e DALHOUSIE UNIVERSITY   (Canada)

^f UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE;

AMINO ACID SUBSTITUTION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG INFORMATION; MALE; MOUSE; NONHUMAN;

EID: 0042890359     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00434-6     Document Type: Article

References (48)

1. (a) Cortes S., Liao Z.-K., Watson D., Kohn H. J. Med. Chem. 28:1985;601
2. (b) Conley J.D., Kohn H. J. Med. Chem. 30:1987;567
3. (c) Kohn H., Conley J.D. Chem. Br. 24:1988;231
4. (d) Kohn H., Conley J.D., Leander J.D. Brain Res. 457:1988;371
5. (d) Kohn H., Conley J.D., Leander J.D. Brain Res. 457:1988;371
6. (e) Kohn H., Sawhney K.N., LeGall P., Conley J.D., Robertson D.W., Leander J.D. J. Med. Chem. 33:1990;919
7. (f) Kohn H., Sawhney K.N., LeGall P., Robertson D.W., Leander J.D. J. Med. Chem. 34:1991;2444
8. g) Kohn H., Sawhney K.N., Bardel P., Robertson D.W., Leander J.D. J. Med. Chem. 36:1993;3350
9. (h) Bardel P., Bolanos A., Kohn H. J. Med. Chem. 37:1994;4567
10. (i) Kohn H., Sawhney K.N., Robertson D.W., Leander J.D. J. Pharm. Sci. 83:1994;689
11. (a) Cortes S., Liao Z.-K., Watson D., Kohn H. J. Med. Chem. 28:1985;601 (b) Conley J.D., Kohn H. J. Med. Chem. 30:1987;567 (c) Kohn H., Conley J.D. Chem. Br. 24:1988;231 (d) Kohn H., Conley J.D., Leander J.D. Brain Res. 457:1988;371 (e) Kohn H., Sawhney K.N., LeGall P., Conley J.D., Robertson D.W., Leander J.D. J. Med. Chem. 33:1990;919 (f) Kohn H., Sawhney K.N., LeGall P., Robertson D.W., Leander J.D. J. Med. Chem. 34:1991;2444 (g) Kohn H., Sawhney K.N., Bardel P., Robertson D.W., Leander J.D. J. Med. Chem. 36:1993;3350 (h) Bardel P., Bolanos A., Kohn H. J. Med. Chem. 37:1994;4567 (i) Kohn H., Sawhney K.N., Robertson D.W., Leander J.D. J. Pharm. Sci. 83:1994;689 (j) Choi D., Stables J.P., Kohn H. J. Med. Chem. 39:1996;1907 (k) LeTiran A., Stables J.P., Kohn H. J. Med. Chem. 45:2002;4762.
12. (a) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Stables J.P. Pharmazie. 3:1996;145 (b) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Winiecka I., Stables J.P. Pharmazie. 51:1996;212 (c) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Winiecka I., Stables J.P. Pharmazie. 55:2000;27 (d) Paruszewski R., Strupinska M., Stables J.P., Swiader M., Czuczwar S., Kleinrock Z., Turski W. Chem. Pharm. Bull. 49:2001;629.
13. (a) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Stables J.P. Pharmazie. 3:1996;145 (b) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Winiecka I., Stables J.P. Pharmazie. 51:1996;212 (c) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Winiecka I., Stables J.P. Pharmazie. 55:2000;27 (d) Paruszewski R., Strupinska M., Stables J.P., Swiader M., Czuczwar S., Kleinrock Z., Turski W. Chem. Pharm. Bull. 49:2001;629.
14. (a) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Stables J.P. Pharmazie. 3:1996;145 (b) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Winiecka I., Stables J.P. Pharmazie. 51:1996;212 (c) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Winiecka I., Stables J.P. Pharmazie. 55:2000;27 (d) Paruszewski R., Strupinska M., Stables J.P., Swiader M., Czuczwar S., Kleinrock Z., Turski W. Chem. Pharm. Bull. 49:2001;629.
15. (a) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Stables J.P. Pharmazie. 3:1996;145 (b) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Jaworski P., Winiecka I., Stables J.P. Pharmazie. 51:1996;212 (c) Paruszewski R., Rostafinska-Suchar G., Strupinska M., Winiecka I., Stables J.P. Pharmazie. 55:2000;27 (d) Paruszewski R., Strupinska M., Stables J.P., Swiader M., Czuczwar S., Kleinrock Z., Turski W. Chem. Pharm. Bull. 49:2001;629.
16. Ho B., Venkatarangan P.M., Cruse S.F., Hinko C.N., Andersen P.H., Crider A.M., Adloo A.A., Roane D.S., Stables J.P. Eur. J. Med. Chem. 33:1998;23.
17. Levy R.H., Mattson R., Meldrum B. Antiepileptic Drugs, 4th ed. 1995;Raven, New York. Chapter 6.
18. Stables, J. P.; Kupferberg, H. J. In Molecular and Cellular Targets for Antiepileptic Drugs; Avanzini, G., Tanganelli, P., Avoli, M., Eds.; John Libbey: London, 1997; p 191.
19. White, H. S.; Woodhead, J. H.; Franklin, M. R. In Antiepileptic Drugs, 4rd ed.; Levy, R. H., Mattson, R. H., Meldrum, B. S., Eds.; Raven: New York, 1995; p 99.
20. LeTiran A., Stables J.P., Kohn H. Bioorg. Med. Chem. 9:2001;2693.
21. Andurkar S.V., Béguin C., Stables J.P., Kohn H. J. Med. Chem. 44:2001;1475.
22. Shen M., LeTiran A., Xiao Y., Golbraikh A., Kohn H., Tropsha A. J. Med. Chem. 45:2002;2811.
23. Dunham M.S., Miya T.A. J. Am. Pharm. Assoc. Sci. Edit. 46:1957;208.
24. Knudsen C.G., Rapoport H. J. Org. Chem. 48:1983;2260.
25. Maurer P.J., Takahata H., Rapoport H. J. Am. Chem. Soc. 106:1984;1095.
26. Chakravarty P.K., Greenlee W.J., Parsons W.H., Patchett A.A., Combs P., Roth A., Busch R.D., Mellin T.N. J. Med. Chem. 32:1989;1886.
27. Deziel R., Plante R., Caron V., Grenier L., Llinas-Burnet M., Duceppe J.S., Malenfant E., Moss N. J. Org. Chem. 61:1996;2901.
28. Koskinen A.M.P., Koskinen P.J. Synlett. 1993;501.
29. Murry J.A., Frantz D.E., Soheili A., Tillyer R., Grabowski E.J., Reider P.J. J. Am. Chem. Soc. 123:2001;9696.
30. Sisko J., Mellinger M., Sheldrake P.W., Baine N.H. Tetrahedron Lett. 37:1996;8113.
31. Jackman, L. M.; Sternhell, S. In Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon: New York, 1969; p 278.
32. Cupps T.L., Boutin R.H., Rapoport H. J. Org. Chem. 50:1985;3972.
33. Boutin R.H., Rapoport H. J. Org. Chem. 51:1986;5320.
34. Andurkar S.V., Stables J.P., Kohn H. Tetrahedron: Asymmetry. 9:1998;3841.
35. (a) Marvell E.N., Li T. Synthesis. 1973;457 (b) Lindlar, H.; Dubuis, R. John Wiley: New York, 1973 Org. Synth., Collective Vol. 5, p 880.
36. (b) Lindlar, H.; Dubuis, R. John Wiley: New York, 1973 Org. Synth., Collective Vol. 5, p 880.
37. 1H NMR analysis showed that the ratio of cis-36 to trans-10 changed from 3.7:1 to approximately 1:1 upon standing at room temperature for 3 months.
38. Pretsch, E.; Simon, W.; Seibl, J.; Clerc, T., In Tables of Spectral Data for Structure Determination of Organic Compounds. 2nd ed.; 1989: Springer: New York; p C188.
39. Porter R.J., Cereghino J.J., Gladding G.D., Hessie B.J., Kupferberg H.J., Scoville B., White B.G. Cleveland Clin. Q. 51:1984;293.
40. Krall R.L., Perry J.K., White B.G., Kupferberg H.J., Swinyard E.A. Epilepsia. 19:1978;409.
41. Schultz T.W., Sinks G.D., Hunter R.S. SAR QSAR Env. Res. 3:1995;27.
42. Hermens J.L.M. Environ. Health Perspect. 87:1990;219.
43. Zhuo J.-C. Mag. Reson. Chem. 35:1997;21.
44. Balsamo A., Crotti P., Lapucci A., Macchia B., Macchia F., Cuttica A., Passerini N. J. Med. Chem. 24:1981;525.
45. Synge R.L.M. Biochem. J. 33:1939;1913.
46. The (S)-isomer of 10 corresponds to the N-acetyl derivative of the natural product merucathione, see: Brenneisen R., Geisshüsler S. J. Nat. Prod. 50:1987;1188.
47. Woodbury D.M., Penry J.K., Pippenger C.E. Antiepileptic Drugs, 2nd ed. 1982;Raven, New York.
48. Finney D.J. Probit Analysis, 3rd ed. 1971;Cambridge University, London.