Arzneimittelforschung 2008; 58(4): 155-159
DOI: 10.1055/s-0031-1296486
CNS-active Drugs · Hypnotics · Psychotropics · Sedatives
Editio Cantor Verlag Aulendorf (Germany)

Synthesis of DL-Fluorobenzenamides as Anticonvulsants

Sergio Enrique Meza-Toledo
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Fabiola Lira-Zárate
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Elsa Lizbeth Robles-Martínez
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Belen Peralta-Alvarez
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Fabiola Cabrera-Cedillo
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Javier Peralta-Cruz
2   Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Claudia Cruz-Peinado
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
,
Humberto Miñón-López
1   Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México, México
› Author Affiliations
Further Information

Publication History

Publication Date:
15 December 2011 (online)

Abstract

DL-2-Hydroxy-2-phenyl butyramide (1, CAS 52839-87-9), DL-3-hydroxy-3-phenyl pentanamide (2, CAS 131802-69-2) and DL-4-hydroxy-4-phenyl hexanamide (3, CAS 67880-30-2) are anticonvulsants. Searching for more active compounds, some DL-fluorobenzenamides were prepared and tested: DL-2-hydroxy-2-(3’-tri-fluoromethylphenyl) butyramide (4), DL-2-Hydroxy-2-4’-trifluoromethylphenyl) butyramide (5, CAS 620950-10-9), DL-2-hydroxy-2-[3’][5’-bis(trifluoromethyl)phenyl]butyramide (6, CAS 620950-09-6), DL-3-hydroxy-3-(3’-trifluoromethylphenyl) pentanamide (7), DL-3-hydroxy-3-(4’-trifluoromethylphenyl)pentanamide (8), and DL-3-hydroxy-3-[3’][5’-bis(trifluoromethyl)phenyl]pentanamide (9, CAS 863976-07-2). Compounds 4-9 exhibited anticonvulsant activity in seizures induced by pentylenetetrazol in mice. Incorporation of trifluoromethyl groups in the phenyl ring of 1, 2 and 3 increased their potency. Compounds 4, 6 and 9 exhibited a similar anticonvulsant activity as the reference drug phenobarbital (CAS 50-06-6).

 
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