Synthesis of DL-hydroxybenzenamides as anticonvulsants.
The anticonvulsant activity of some DL-hydroxybenzenamides is described. The following compounds from this series were prepared and tested: DL-2-hydroxy-2-(3'-bromophenyl)butyramide (4, CAS 620950-12-1), DL-2-hydroxy-2-(4'-bromophenyl)butyramide (5, CAS 620950-13-2), DL-2-hydroxy-2-(3'-nitrophenyl)butyramide (6, CAS 620950-14-3), DL-2-hydroxy-2-phenyl hexanamide (7, CAS 63002-05-1), DL-2-hydroxy-2-(3',4'-dichlorophenyl)hexanamide (8, CAS 863976-06-1), DL-3-hydroxy-3-(4'-bromophenyl)pentanamide (9, CAS 620950-16-5), DL-3-hydroxy-3-phenyl-heptanamide (10, CAS 863976-08-3) and DL-4-hydroxy-4-(4'-bromophenyl)hexanamide (11,CAS 620950-18-7). Compounds 4, 5, 9 and 11 exhibited significant activity in seizures induced by pentylenetetrazol. Incorporation of bromine in the phenyl ring increased their potency. Compounds 4, 5, 9 and 11 exhibited a similar anticonvulsant activity as the reference drug phenobarbital (CAS 50-06-6).
Meza-Toledo
Sergio E
SE
Departamento de Bioquímica, Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, México DF, México. smezat@ipn.mx
Yasutake-Kimoto
Liliana
L
Alcalá-Rentería
Martha
M
Domínguez-Rodríguez
Miguel A
MA
Jaime-Rodríguez
Rodrigo
R
Nava-Arzaluz
María G
MG
Gutiérrez-Laflor
Giovanna
G
Peralta-Cruz
Javier
J
Carvajal-Sandoval
Guillermo
G
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D003292:Convulsants; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D010433:Pentylenetetrazole; D012640:Seizures / Q000139:chemically induced / Q000517:prevention & control; D013055:Spectrophotometry, Infrared
D000927:Anticonvulsants; D001549:Benzamides; D003292:Convulsants; D007202:Indicators and Reagents; D010433:Pentylenetetrazole