Stereoselective anticonvulsant activity of the enantiomers of (±)-2-hydroxy-2-phenylbutyramide

S. E. Meza-Toledo, C. Ortega-Gonzalez, E. Juarez-Carvajal, G. Carvajal-Sandoval

Research output: Contribution to journalArticleResearchpeer-review

8 Citations (Scopus)

Abstract

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.
Original languageAmerican English
Pages (from-to)756-759
Number of pages680
JournalArzneimittel-Forschung/Drug Research
StatePublished - 1 Jan 1995

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anticonvulsants
Enantiomers
enantiomers
Anticonvulsants
Rotarod Performance Test
Phenethylamines
Pentylenetetrazole
Acids
Quinine
Ataxia
Chloroform
Ammonia
Amides
ataxia
seizures
Seizures
Salts
High Pressure Liquid Chromatography
acids
Chlorine compounds

Cite this

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title = "Stereoselective anticonvulsant activity of the enantiomers of (±)-2-hydroxy-2-phenylbutyramide",
abstract = "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.",
author = "Meza-Toledo, {S. E.} and C. Ortega-Gonzalez and E. Juarez-Carvajal and G. Carvajal-Sandoval",
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language = "American English",
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journal = "Arzneimittel-Forschung/Drug Research",
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Stereoselective anticonvulsant activity of the enantiomers of (±)-2-hydroxy-2-phenylbutyramide. / Meza-Toledo, S. E.; Ortega-Gonzalez, C.; Juarez-Carvajal, E.; Carvajal-Sandoval, G.

In: Arzneimittel-Forschung/Drug Research, 01.01.1995, p. 756-759.

Research output: Contribution to journalArticleResearchpeer-review

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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.

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