(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity

Abstract

Ester based on l-menthol and phenibut ‒ (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride was obtained in 78% yield using N,N′-dicyclohexylcarbodiimide as a coupling reagent along with catalytic amount of 4-dimethylaminopyridine. The obtained product was characterized by FT-IR, fast-atom bombardment-mass spectrometry along with 1H-NMR and 13C-NMR spectral analysis; the purity was assessed using high-performance liquid chromatography. Phenibut ester has been examined on the models of chemically- and electrically-induced seizures for potential anticonvulsant profile.

Keywords

• ester
• l-menthol
• phenibut
• terpenoid
• anticonvulsant activity
• steglich esterification