(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
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 character...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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De Gruyter
2022-07-01
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| Series: | Open Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/chem-2022-0189 |
| _version_ | 1811236472507858944 |
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| author | Nesterkina Mariia Musatov Vladimir Honcharova Olena Kravchenko Iryna |
| author_facet | Nesterkina Mariia Musatov Vladimir Honcharova Olena Kravchenko Iryna |
| author_sort | Nesterkina Mariia |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T12:10:26Z |
| format | Article |
| id | doaj.art-a068a88b3bb84af1990c1370b525cf9b |
| institution | Directory Open Access Journal |
| issn | 2391-5420 |
| language | English |
| last_indexed | 2024-04-12T12:10:26Z |
| publishDate | 2022-07-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Open Chemistry |
| spelling | doaj.art-a068a88b3bb84af1990c1370b525cf9b2022-12-22T03:33:36ZengDe GruyterOpen Chemistry2391-54202022-07-0120170370710.1515/chem-2022-0189(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activityNesterkina Mariia0Musatov Vladimir1Honcharova Olena2Kravchenko Iryna3Department of Pharmacology and Pharmacy, Odessa International Medical University, Kanatna Street 99, 65000 Odessa, UkraineDivision of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Avenue 60, 61072 Kharkiv, UkraineLLC Cotecna Ukraine Limited, Liustdorfska Doroga Str., 140-A, 65114 Odessa, UkraineLaboratory of Medical Bioclimatology, State Enterprise Ukrainian Research Institute for Medicine of Transport, Ministry of Health of Ukraine, Kanatna Street 92, 65039 Odessa, UkraineEster 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.https://doi.org/10.1515/chem-2022-0189esterl-mentholphenibutterpenoidanticonvulsant activitysteglich esterification |
| spellingShingle | Nesterkina Mariia Musatov Vladimir Honcharova Olena Kravchenko Iryna (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity Open Chemistry ester l-menthol phenibut terpenoid anticonvulsant activity steglich esterification |
| title | (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity |
| title_full | (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity |
| title_fullStr | (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity |
| title_full_unstemmed | (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity |
| title_short | (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity |
| title_sort | 1r 2s 5r 5 methyl 2 propan 2 yl cyclohexyl 4 amino 3 phenylbutanoate hydrochloride synthesis and anticonvulsant activity |
| topic | ester l-menthol phenibut terpenoid anticonvulsant activity steglich esterification |
| url | https://doi.org/10.1515/chem-2022-0189 |
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