Browse > Article

Design, Synthesis and Anticonvulsive Activities of Potential Prodrugs Linked by Two-carbon Chain  

Zhao, Long-Xuan (College of Pharmacy, Yeungnam University)
Moon, Yoon-Soo (College of Pharmacy, Yeungnam University)
Basnet, Ar-Jun (College of Pharmacy, Yeungnam University)
Park, Jae-Gyu (College of Pharmacy, Yeungnam University)
Kim, Eun-kyung (College of Pharmacy, Yeungnam University)
Kim, Dae-Ok (College of Pharmacy, Yeungnam University)
Jeong, Tae-Cheon (College of Pharmacy, Yeungnam University)
Jahng, Yurng-Dong (College of Pharmacy, Yeungnam University)
Choi, Jong-Won (College of Pharmacy, Kyungsung University)
Lee, Eung-Seok (College of Pharmacy, Yeungnam University)
Publication Information
Archives of Pharmacal Research / v.26, no.10, 2003 , pp. 785-795 More about this Journal
Abstract
For the development of new anticonvulsive agents, GABAmimetics such as nipecotic acid, isonipecotic acid, ${\gamma}-aminobutyric$ acid (GABA), ${\gamma}-vinyl$ GABA (vigabatrin) and valproic acid were covalently coupled through an ester bond by a two-carbon linker chain as potential prodrugs and evaluated for their anticonvulsive activities.
Keywords
Anticonvulsants; Prodrugs; Synthesis; Linker chain; Anticonvulsive activities;
Citations & Related Records

Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Jacob, J. N., Shashoua, V. E., Campbell, A., and Baldessarini, R. J., Gamma-aminobutyric acid esters 2. Synthesis, brain uptake, and pharmacological properties of lipid esters of gamma-aminobutyric acid. J. Med. Chem., 28, 106-110 (1985)   DOI   PUBMED
2 Kim, Y. c., Zhao, L. X., Kim, T. H., Je, S. m., Kim, E. k., Choi, H., Chae, W. G., Park, M., Choi, J., Jahng, Y., and Lee, E. S., Design and synthesis of anticonvulsive agents as $\gamma$-vinyl GABA-based potential dual acting prodrugs and their biological activities. Bioorg. Med. Chem. Lett., 10, 609-613 (2000)   DOI   PUBMED   ScienceOn
3 Kohn, H., Sawhney, K. N., LeGall, P., Conley, J. D., Robertson, D. W., and Leander, J. D., Preparation and anticonvulsant activity of a series of functionalized alpha-aromatic and alpha-heteroaromatic amino acids. J. Med. Chem., 33, 919-926 (1990)   DOI   PUBMED
4 Lin, S. S. and Sun, L. R., SGB-017 (ADCI): A Novel Anticonvulsant with a Dual Mechanism of Action. CNS Drug Reviews, 5(4), 365-378 (1999)   DOI   ScienceOn
5 Son, K., Jung, K., Kim, M., Lee, J., Choi, J., Lee, E. S., and Park, M., The effect of N-alkyloxycarbonyl group on the anticonvulsant activities of N-alkyloxycarbonyl-$\alpha$-aminoglutarimides. Arch. Pharm. Res., 21(6), 764-768 (1998)   DOI   ScienceOn
6 Kwon, C. H., Iqbal, M. T., and Wurpel, J. N. D., Synthesis and anticonvulsant activity of 2-iminohydantoins. J. Med. Chem., 34, 1845-1849 (1991)   DOI
7 Edafiogho, I. O., Scott, K. R., Moore, J. A., Farrar, V. A., and Nicholson, J. M., Synthesis and anticonvulsant activity of imidooxy derivatives. J. Med. Chem., 34, 387-392 (1991)   DOI   PUBMED
8 Maynert, E. W. and Kaji, H. K., On the relationship of brain$\gamma$-amino butyric acid to convulsions. J. Pharmacol. Exp. Ther., 137, 114-121 (1962)   PUBMED
9 Sasaki, H., Mori, Y., Nakamura, J., and Shibasaki, J., Synthesis and anticonvulsant activity of 1-acyl-2-pyrrolidinone derivatives. J. Med. Chem., 34, 628-633 (1991)   DOI   PUBMED
10 Dichter, M. A. and Ayala, G. F., Cellular mechanisms of epilepsy: a status report. Science, 237, 157-164 (1987)   DOI   PUBMED
11 Lee, J., Son, K., Kim, M., Jung, G., Choi, J., Lee, E. S., and Park, M., The effect of N-substituted alkyl groups on anticonvulsant activities of N-Cbz-$\alpha$-amino-N-alkylglutarimides. Arch. Pharm. Res., 22(5), 491-495 (1999)   DOI   ScienceOn
12 Swinyard, E. A., Woodhead, J. H., White, H. S., and Franklin, M. R., General Principles, Experimental Section, Quantification and Evaluation of Anticonvulsants in Antiepileptic Drugs. 3rd Ed. R. Levy, Ed. New York, Ravan Press, p. 88 (1989)
13 Kohn, H., Sawhney, K. N., LeGall, P., Robertson, D. W., and Leander, J. D., Preparation and anticonvulsant activity of a series of functionalized alpha-heteroatom-substituted amino acids. J. Med. Chem., 34, 2444-2452 (1991)   DOI   PUBMED
14 Jackson, J., Alan, E., Johnston, A., and Robert, A. W., Rapid, selective removal of benzyloxycarbonyl groups from peptides by catalytic transfer hydrogenation. Synthesis, 10, 685-687 (1976)
15 Jung, K., Son, K., Kim, M., Lee, J., Choi, J., Lee, E. S., and Park, M., The effect of N-alkyloxycarbonyl group on the anticonvulsant activities of N-alkyloxycarbonyl-a-amino-Nmethylsuccinimides. Arch. Pharm. Res., 21(6), 759-763 (1998)   DOI   ScienceOn
16 Krall, R. L., Penry, J. K., White, B. G., Kupferberg, H. J., and, Swinyard, E. A., Antiepileptic drug development: II. Anticonvulsant drug screening. Epilepsia, 19, 409-428 (1978)   DOI   ScienceOn
17 Smith, M. B. and Kwon, T. W., Preparation of 5-alkenyl- and 5-dienyl-2-pyrrolinone derivatives. Synth. Commu., 22, 2865-2873 (1992)   DOI   ScienceOn
18 Frey, H. H. and Loscher, W., Cetyl GABA: Effect on convulsant thresholds in mice and acute toxicity. Neuropharmacology, 19, 217-220 (1980)   DOI   ScienceOn
19 Holland, K. D., McKeon, A. C., Canney, D. J., Covey, D. F., and Ferrendelli, J. A., Relative anticonvulsant effects of GABA-mimetics and GABA modulatory agents. Epilepsia, 33, 981-986 (1992)   DOI   ScienceOn
20 Shashoua, V. E., Jacob, J. N., Ridge, R., Campbell, A., and Baldessarini, R. J., Gamma-aminobutyric acid esters 1. Synthesis, brain uptake, and pharmacological studies of aliphatic and steroid esters of gamma-aminobutyric acid. J. Med. Chem., 27, 659-664 (1984)   DOI   PUBMED
21 Matsuyama, K., Gomita, Y., and Yamashita, C., Evaluation of isonicotinyl $\gamma$-amino butyric acid (GABA) and nicotinyl-GABA as pro-drugs of GABA. Chem. Pharm. Bull., 32, 4089-4095 (1984)   DOI   PUBMED   ScienceOn
22 Krogsgaard-Larsen, P., $\gamma$-Aminobutyric acid agonist, antagonist and uptake inhibitors, design and therapeutic aspects. J. Med. Chem., 24, 1377-1383 (1981)   DOI   PUBMED