Carbamate derivatives of felbamate as potential anticonvulsant agents

Medicinal Chemistry Research

Volumn 19, Issue 5, 2010, Pages 498-513

  Kung, Ching Hsin ^a   Kwon, Chul Hoon ^a  

^a ST JOHN'S UNIVERSITY   (United States)

Author keywords

Anticonvulsant; Carbamate; Felbamate

Indexed keywords

2 PHENYLBUTYL CARBAMATE; ANTICONVULSIVE AGENT; BURAMATE; CARBAMIC ACID DERIVATIVE; FELBAMATE; MEPROBAMATE; N,O DIBENZYL CARBAMATE; NITROGEN; O BENZYL N (1 HYDROXYMETHYLBUTYL)CARBAMATE; O BENZYL N (1) 2 HYDROXY 1 METHYLETHYL CARBAMATE; O BENZYL N (1) 2 HYDROXYMETHYLPROPYL CARBAMATE; O BENZYL N (2 HYDROXYETHYL)CARBAMATE; O BENZYL N 1 BENZYL 2 HYDROXYETHYL CARBAMATE; O BENZYL N 2 HYDROXY 1 METHYLETHYL CARBAMATE; OXYGEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; QUANTITATIVE ANALYSIS; RAT; STRUCTURE ACTIVITY RELATION;

EID: 77953323575     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-009-9208-6     Document Type: Article

References (16)

1. M Aurousseau 1960 Comparative study of some pharmacodynamic and physicochemical properties of 2-thiophene derivatives, N-(2-thenyl)-acetamide and the thenylurethane of glycol and their benzene isosteres Arch Int Pharmacodyn Ther 127 220 247 1:CAS:528:DyaF3MXotlWhsw%3D%3D 13685181
2. Dieckhaus CM, Macdonald TL (2001) The metabolism and idiosyncratic reactions of the antiepileptic drug felbamate. In: Dissertation abstracts, vol 62-01B, 219 pp
3. CM Dieckhaus WL Santos RD Sofia TL Macdonald 2001 The chemistry, toxicology, and identification in rat and human urine of 4-hydroxy-5-phenyl-1,3- oxazaperhydroin-2-one: a reactive metabolite in felbamate bioactivation Chem Res Toxicol 14 958 964 10.1021/tx000139n 10.1021/tx000139n 1:CAS:528: DC%2BD3MXkvFSjtbs%3D 11511169 (Pubitemid 32800151)
4. H-H Frey I Bartels 1997 Felbamate and meprobamate: a comparison of their anticonvulsant properties Epilepsy Res 27 151 164 10.1016/S0920-1211(97)01021-8 10.1016/S0920-1211(97)01021-8 1:CAS:528:DyaK2sXltVShtbk%3D 9237049 (Pubitemid 27306797)
5. 2OH) Ann Pharm Fr 9 6 390 397 1:CAS:528:DyaG38XmsV2m 14885835
6. Kupferberg HJ (1995) Felbamate. In: Levy RH et al (eds) Antiepileptic drugs, 4th edn. Raven Ress, New York, pp 791-827
7. BJ Ludwing LS Powell FM Berger 1969 Carbamate derivatives related to meprobamate J Med Chem 12 462 472 10.1021/jm00303a029 10.1021/jm00303a029
8. Murray WJ, Kier LB (1977) Noncyclic anticonvulsants. In: Vida JA (ed) Medicinal chemistry, vol 15. Anticonvulsants. Academic Press, New York, pp 578-619
9. RJ Parker NR Hartman BA Roecklein H Mortko HJ Kupferberg J Stables JM Strong 2005 Stability and comparative metabolism of selected felbamate metabolites and postulated fluorofelbamate metabolites by postmitochondrial suspensions Chem Res Toxicol 18 1842 1848 10.1021/tx050130r 10.1021/tx050130r 1:CAS:528:DC%2BD2MXht1eitrnP 16359174 (Pubitemid 43023042)
10. RJ Porter JJ Cereghino GD Gladding BJ Hessie HJ Kupferberg B Scoville BG White 1984 Antiepileptic drug development program Cleve Clin Q 51 293 305 1:STN:280:DyaL2c3otlehuw%3D%3D 6380818
11. P Sieber B Iselin 1968 Peptidsynthesen unter Verwendung der 2-(p-Diphenyl)-isopropyl-oxycarbonyl (Dpoc)-Aminoschutzgruppe Helv Chim Acta 51 4 622 632 1:CAS:528:DyaF1cXktFSlu7Y%3D 5683980
12. M Tanaka K Horisaka C Yamagami N Takao T Fujita 1985 Quantitative structure-activity relationships of anticonvulsant aralkyl and alkyl carbamates Chem Pharm Bull (Tokyo) 33 6 2403 2410 1:CAS:528:DyaL2MXltFGlurY%3D
13. CD Thompson MT Kinter TL Macdonald 1996 Synthesis and in vitro reactivity of 3-carbamoyl-2-phenylpropionaldehyde and 2-phenylpropenal: putative reactive metabolites of felbamate Chem Res Toxicol 9 1225 1229 10.1021/tx9601566 10.1021/tx9601566 1:CAS:528:DyaK28Xms1Crtrc%3D 8951223 (Pubitemid 26403826)
14. CD Thompson TA Miller MT Barthen CM Dieckhaus RD Sofia TL Macdonald 2000 The synthesis, in vitro reactivity, and evidence for formation in humans of 5-phenyl-1,3-oxazinane-2,4-dione, a metabolite of felbamate Drug Metab Dispos 28 4 434 439 1:CAS:528:DC%2BD3cXitFeqsbY%3D 10725312
15. SS Wang RB Merrifield 1969 Preparation of some new biphenylisopropyl- oxycarbonyl amino acids and their application to the solid phase synthesis of a tryptophan-containing heptapeptide of bovine parathyroid hormone Int J Protein Res 1 235 244 1:CAS:528:DyaE3cXmslalsg%3D%3D 5408675
16. C Yamagami C Sonoda N Takao M Tanaka J Yamada K Horisaka T Fujita 1982 A quantitative structure-activity study of anticonvulsant benzyl N,N-dimethyl carbamates Chem Pharm Bull (Tokyo) 30 11 4175 4180 1:CAS:528: DyaL3sXotlagsQ%3D%3D