TY - JOUR
T1 - Stereoselective anticonvulsant activity of the enantiomers of (±)-2-hydroxy-2-phenylbutyramide
AU - Meza-Toledo, S. E.
AU - Ortega-Gonzalez, C.
AU - Juarez-Carvajal, E.
AU - Carvajal-Sandoval, G.
PY - 1995
Y1 - 1995
N2 - The enantiomers of the anticonvulsant DL-2-hydroxy-2-phenylbutyramide (1) were prepared by resolving the (-)-quinine and (+)-1-phenylethylamine salts of the acids. The optically active acids were then esterified and reacted with ammonia to give (+)-1 and (-)-1. Optical purity of the amides was greater than 99.9% enantiomeric excess by chiral HPLC. Examination of the infrared spectra of the enantiomers and the racemate of 1 in chloroform solution showed identical spectra, but the spectrum of the racemate in a KBr disc was somewhat different from those of the pure enantiomers. Pharmacologically, 1 and its enantiomers have a similar significant anticonvulsant activity at peak drug effect against pentylenetetrazol seizures, but a variation in the time between the enantiomers was found with the anticonvulsant activity. In the rotarod ataxia test (-)-1-possessed the lowest neurotoxicity.
AB - The enantiomers of the anticonvulsant DL-2-hydroxy-2-phenylbutyramide (1) were prepared by resolving the (-)-quinine and (+)-1-phenylethylamine salts of the acids. The optically active acids were then esterified and reacted with ammonia to give (+)-1 and (-)-1. Optical purity of the amides was greater than 99.9% enantiomeric excess by chiral HPLC. Examination of the infrared spectra of the enantiomers and the racemate of 1 in chloroform solution showed identical spectra, but the spectrum of the racemate in a KBr disc was somewhat different from those of the pure enantiomers. Pharmacologically, 1 and its enantiomers have a similar significant anticonvulsant activity at peak drug effect against pentylenetetrazol seizures, but a variation in the time between the enantiomers was found with the anticonvulsant activity. In the rotarod ataxia test (-)-1-possessed the lowest neurotoxicity.
KW - DL-2-hydroxy-2-phenylbutyramide enantiomers, pharmacology, synthesis
KW - anticonvulsants, chiral
UR - http://www.scopus.com/inward/record.url?scp=0029012423&partnerID=8YFLogxK
M3 - Artículo
SN - 0004-4172
VL - 45
SP - 756
EP - 759
JO - Arzneimittel-Forschung/Drug Research
JF - Arzneimittel-Forschung/Drug Research
IS - 7
ER -