Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol
The present work describes the synthesis, physico-chemical characteristics, antioxidative properties, and high-performance liquid chromatography (HPLC) enantioseparation of novel, potentially bioactive aryloxyaminopropanols – derivatives of naphthalen-2-ol modified in the basic part of their molecul...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Sciendo
2023-09-01
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| Series: | European Pharmaceutical Journal |
| Subjects: | |
| Online Access: | https://doi.org/10.2478/afpuc-2023-0015 |
| _version_ | 1797303147277844480 |
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| author | Čižmáriková R. Habala L. Valentová J. Némethy A. Bruchatá K Hroboňová K. |
| author_facet | Čižmáriková R. Habala L. Valentová J. Némethy A. Bruchatá K Hroboňová K. |
| author_sort | Čižmáriková R. |
| collection | DOAJ |
| description | The present work describes the synthesis, physico-chemical characteristics, antioxidative properties, and high-performance liquid chromatography (HPLC) enantioseparation of novel, potentially bioactive aryloxyaminopropanols – derivatives of naphthalen-2-ol modified in the basic part of their molecules. Reaction of naphthalene-2-ol with chloromethyloxirane leads to 2-[(naphthalen-2-yloxy)methyl]oxirane, which reacts in the next step with branched aliphatic amines (isopropylamine, tert-butylamine, and dimethylamine), aromatic amines (aniline, 3,4-dimethoxyphenylethylamine), and heterocyclic amines (pyrrolidine, imidazole, 2-methylimidazole, piperidine, morpholine, 4-methylpiperidine, or 2-methoxyphenylpiperidine). The target compounds were isolated in the form of free bases, as well as their salts with fumaric or hydrochloric acid. Their purity was established by thin-layer chromatography and their IR, UV, 1H-NMR, and 13C-NMR spectra were recorded. The antioxidant activities of prepared compounds were measured by the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method and they were compared with the values for the corresponding salts. Enantioseparation was accomplished by means of enantioselective HPLC using amylose tris(3,5-dimethylphenyl)carbamate (Chiralpak AD), as well as Chirobiotic T (native teicoplanin) in some cases. |
| first_indexed | 2024-03-07T23:48:45Z |
| format | Article |
| id | doaj.art-024e0fa86e7c4c4e99fbbee30a43c608 |
| institution | Directory Open Access Journal |
| issn | 2453-6725 |
| language | English |
| last_indexed | 2024-03-07T23:48:45Z |
| publishDate | 2023-09-01 |
| publisher | Sciendo |
| record_format | Article |
| series | European Pharmaceutical Journal |
| spelling | doaj.art-024e0fa86e7c4c4e99fbbee30a43c6082024-02-19T09:03:14ZengSciendoEuropean Pharmaceutical Journal2453-67252023-09-01702203010.2478/afpuc-2023-0015Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-olČižmáriková R.0Habala L.1Valentová J.2Némethy A.3Bruchatá K4Hroboňová K.5Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, BratislavaDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, BratislavaDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, BratislavaDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, BratislavaDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, BratislavaInstitute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in BratislavaThe present work describes the synthesis, physico-chemical characteristics, antioxidative properties, and high-performance liquid chromatography (HPLC) enantioseparation of novel, potentially bioactive aryloxyaminopropanols – derivatives of naphthalen-2-ol modified in the basic part of their molecules. Reaction of naphthalene-2-ol with chloromethyloxirane leads to 2-[(naphthalen-2-yloxy)methyl]oxirane, which reacts in the next step with branched aliphatic amines (isopropylamine, tert-butylamine, and dimethylamine), aromatic amines (aniline, 3,4-dimethoxyphenylethylamine), and heterocyclic amines (pyrrolidine, imidazole, 2-methylimidazole, piperidine, morpholine, 4-methylpiperidine, or 2-methoxyphenylpiperidine). The target compounds were isolated in the form of free bases, as well as their salts with fumaric or hydrochloric acid. Their purity was established by thin-layer chromatography and their IR, UV, 1H-NMR, and 13C-NMR spectra were recorded. The antioxidant activities of prepared compounds were measured by the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method and they were compared with the values for the corresponding salts. Enantioseparation was accomplished by means of enantioselective HPLC using amylose tris(3,5-dimethylphenyl)carbamate (Chiralpak AD), as well as Chirobiotic T (native teicoplanin) in some cases.https://doi.org/10.2478/afpuc-2023-0015β-sympatolytikáaryloxyaminopropanolypropranololnadolollevobunololantiradikálová aktivitahplc-enantioseparácia |
| spellingShingle | Čižmáriková R. Habala L. Valentová J. Némethy A. Bruchatá K Hroboňová K. Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol European Pharmaceutical Journal β-sympatolytiká aryloxyaminopropanoly propranolol nadolol levobunolol antiradikálová aktivita hplc-enantioseparácia |
| title | Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol |
| title_full | Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol |
| title_fullStr | Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol |
| title_full_unstemmed | Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol |
| title_short | Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol |
| title_sort | synthesis antioxidant activity and hplc enantioseparation of aryloxyaminopropanols derived from naphthalen 2 ol |
| topic | β-sympatolytiká aryloxyaminopropanoly propranolol nadolol levobunolol antiradikálová aktivita hplc-enantioseparácia |
| url | https://doi.org/10.2478/afpuc-2023-0015 |
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