Synthesis, antimicrobial and antiradical activity of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones, intermediates of biologically active compounds and activity comparison with 3-(alkoxymethyl)-4-(alkylamino-2-hydroxypropoxyphenyl)alkanones type of beta blockers

European Pharmaceutical Journal Pub Date : 2020-05-01 DOI:10.2478/afpuc-2020-0012

R. Čižmáriková, M. Markuliak, L. Habala, J. Valentová, A. Bilková

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引用次数: 2

Abstract

Abstract A homologous series of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones was prepared by the reaction of (3-chloromethyl-4-hydroxyphenyl)propan-1-ones with the corresponding alcohols (methanol – decan-1-ol, propan-2-ol, 2-methylpropan-1-ol, 3-methylbutan-1-ol, cyclopentanol, benzylalcohol) in the presence of sodium hydrogen carbonate. The composition of the synthesised compounds was elucidated by IR, UV and 1H-NMR and 13C-NMR spectra. Selected compounds were tested against human pathogens: gram-positive bacterium Staphylococcus aureus (CNCTC Mau 29/58), gram-negative bacterium Escherichia coli (CNCTC 377/79) and yeast Candida albicans (CCM 8186). Their antimicrobial activities were expressed as minimum inhibitory concentrations. Antioxidant activity was determined using DPPH and ABTS.+ methods. It could be shown that both biological activities, antimicrobial and antioxidant, were lower in comparison with the (2RS)-bis [3-(4-acetyl-2-propoxymethyl)phenoxy-2-hydroxypropyl]isopropylammonium fumarate type of beta blockers.

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生物活性化合物中间体（3-烷氧基甲基-4-羟基苯基）丙-1-酮的合成、抗菌和抗自由基活性以及与3-（烷氧基乙基）-4-（烷基氨基-2-羟基苯基）烷酮类β受体阻滞剂的活性比较

摘要在碳酸氢钠存在下，（3-氯甲基-4-羟基苯基）丙-1-酮与相应的醇（甲醇-癸-1-醇、丙-2-醇、2-甲基丙-1-醇、3-甲基丁-1-醇、环戊醇、苄醇）反应，制备了一系列同源的（3-烷氧基甲基-4-羟基苯）丙-1-酮类化合物。通过IR、UV、1H-NMR和13C-NMR光谱对合成的化合物的组成进行了鉴定。选定的化合物对人类病原体进行了测试：革兰氏阳性细菌金黄色葡萄球菌（CNCTC Mau 29/58）、革兰氏阴性细菌大肠杆菌（CNCTC377/79）和白色念珠菌（CCM 8186）。它们的抗菌活性以最低抑制浓度表示。使用DPPH和ABTS测定抗氧化活性。+方法。可以表明，与富马酸异丙基铵型β受体阻滞剂相比，（2RS）-双[3-（4-乙酰基-2-丙氧基甲基）苯氧基-2-羟丙基]异丙基铵的抗微生物和抗氧化活性均较低。

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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.