Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol

European Pharmaceutical Journal Pub Date : 2023-09-13 DOI:10.2478/afpuc-2023-0015

R. Čižmáriková, L. Habala, J. Valentová, A. Némethy, K Bruchatá, K. Hroboňová

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引用次数: 0

Abstract

Abstract 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, 1 H-NMR, and 13 C-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.

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萘-2-醇基芳氧胺丙醇的合成、抗氧化活性及高效液相色谱对映体分离

摘要:本文研究了具有潜在生物活性的新型萘-2-醇衍生物的合成、理化性质、抗氧化性能和高效液相色谱(HPLC)对映体分离。萘-2-醇与氯甲基氧乙烷反应生成2-[(萘-2-酰基)甲基]氧乙烷，下一步与支链脂肪胺(异丙胺、叔丁胺和二甲胺)、芳香胺(苯胺、3,4-二甲氧基苯乙胺)和杂环胺(吡咯烷、咪唑、2-甲基咪唑、哌啶、啉、4-甲基哌啶或2-甲氧基苯哌啶)反应。目标化合物以游离碱的形式分离，以及它们的盐与富马酸或盐酸。用薄层色谱法确定了它们的纯度，并记录了它们的IR、UV、1h - nmr和13c - nmr光谱。用2,2′-氮基-双(3-乙基苯并噻唑啉-6-磺酸(ABTS)法测定了所制化合物的抗氧化活性，并与相应盐类的测定值进行了比较。对映体分离是通过使用直链淀粉三(3,5-二甲基苯基)氨基甲酸酯(Chiralpak AD)和Chirobiotic T(天然teicoplanin)在某些情况下使用对映体选择性HPLC完成的。

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来源期刊

European Pharmaceutical Journal Pharmacology, Toxicology and Pharmaceutics-Pharmacology, Toxicology and Pharmaceutics (all)

CiteScore

0.60

自引率

0.00%

发文量

期刊介绍： European Pharmaceutical Journal publishes only original articles not previously published and articles that are not being considered or have not been submitted for publication elsewhere. If parts of the results have been published as conference abstract or elsewhere, it should be stated in references. The ethical standards of the Helsinki-Tokio Declaration should be kept. This should be mentioned in the Methods of manuscript. Reviews are published only on request. Authors, whose submitted research work was performed with the support of a company, should indicate this in Conflict of Interest.