M. Michalík, Monika Biela, D. Cagardová, Vladimír Lukes
Abstract Systematic quantum chemical investigation of quercetin and selected eight mono- and bihydroxyflavonols is presented. Structural analysis based on the Density Functional Theory showed that the energetically preferred conformation of flavonols substituted at the C5 and C3 atoms by a hydroxyl group is stabilised via intramolecular hydrogen bonds occurring between the (C4)O···HO(3 or 5) atomic pairs. Depending on the hydroxyl group positions, energetically preferred torsional orientation of the phenyl ring with respect to the planar benzo-γ-pyrone moiety changed from 0 to 180 degrees. Gas-phase electron transitions were investigated using the time-dependent DFT treatment. The dependence of maximal wavelengths on the torsional deformation of the phenyl ring is of a similar shape, i.e. minima observed for the perpendicular orientation and maxima for the planar one. Shape and energies of the Highest Occupied (HOMO) and Lowest Unoccupied (LUMO) Molecular Orbitals were compared. The obtained theoretical results were compared with available experimental data.
{"title":"Influence of catecholic ring torsion on hydroxyflavones","authors":"M. Michalík, Monika Biela, D. Cagardová, Vladimír Lukes","doi":"10.2478/acs-2020-0008","DOIUrl":"https://doi.org/10.2478/acs-2020-0008","url":null,"abstract":"Abstract Systematic quantum chemical investigation of quercetin and selected eight mono- and bihydroxyflavonols is presented. Structural analysis based on the Density Functional Theory showed that the energetically preferred conformation of flavonols substituted at the C5 and C3 atoms by a hydroxyl group is stabilised via intramolecular hydrogen bonds occurring between the (C4)O···HO(3 or 5) atomic pairs. Depending on the hydroxyl group positions, energetically preferred torsional orientation of the phenyl ring with respect to the planar benzo-γ-pyrone moiety changed from 0 to 180 degrees. Gas-phase electron transitions were investigated using the time-dependent DFT treatment. The dependence of maximal wavelengths on the torsional deformation of the phenyl ring is of a similar shape, i.e. minima observed for the perpendicular orientation and maxima for the planar one. Shape and energies of the Highest Occupied (HOMO) and Lowest Unoccupied (LUMO) Molecular Orbitals were compared. The obtained theoretical results were compared with available experimental data.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"49 - 55"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44335107","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract Marigold flowers (Tagetes patula and Calendula officinalis) were chosen for analysis because they are the most often used source of lutein and its isomer zeaxanthin for the production of food supplements on the Czech market. Direct extraction and extraction with alkaline hydrolysis were compared to detect free or bound carotenoids. For carotenoid separation, C18 and C30 columns were used. A new method for determination of carotenoid content in food supplements in form of capsules has been developed and validated. All matrices were analysed by high-performance liquid chromatography with diode array detection (HPLC-DAD). It has been found that alkaline hydrolysis is required for both Marigold flowers and food supplements to release lutein from ester bonds to fatty acids. In Calendula officinalis lutein in the concentration of 807—1472 mg·kg−1 of dry matter was detected. Tagetes patula has been identified as a better lutein source with the content of 5906—8677 mg·kg−1 of dry matter. It has been found that the content of lutein and zeaxanthin in commercial food supplements (Lutein Complex Premium and Occutein Brillant) is consistent with the declared quantity. Linearity of the HPLC-DAD method ranged from 0.1—20 μg·mL−1 with the limit of quantification (LOQ) of 1.7 mg·kg−1 for lutein in Marigold flowers and 200 mg·kg−1 in food supplements. Repeatability was 2.3 % for lutein in all tested matrices.
{"title":"Determination of carotenoids in flowers and food supplements by HPLC-DAD","authors":"P. Pavelková, A. Krmela, V. Schulzova","doi":"10.2478/acs-2020-0002","DOIUrl":"https://doi.org/10.2478/acs-2020-0002","url":null,"abstract":"Abstract Marigold flowers (Tagetes patula and Calendula officinalis) were chosen for analysis because they are the most often used source of lutein and its isomer zeaxanthin for the production of food supplements on the Czech market. Direct extraction and extraction with alkaline hydrolysis were compared to detect free or bound carotenoids. For carotenoid separation, C18 and C30 columns were used. A new method for determination of carotenoid content in food supplements in form of capsules has been developed and validated. All matrices were analysed by high-performance liquid chromatography with diode array detection (HPLC-DAD). It has been found that alkaline hydrolysis is required for both Marigold flowers and food supplements to release lutein from ester bonds to fatty acids. In Calendula officinalis lutein in the concentration of 807—1472 mg·kg−1 of dry matter was detected. Tagetes patula has been identified as a better lutein source with the content of 5906—8677 mg·kg−1 of dry matter. It has been found that the content of lutein and zeaxanthin in commercial food supplements (Lutein Complex Premium and Occutein Brillant) is consistent with the declared quantity. Linearity of the HPLC-DAD method ranged from 0.1—20 μg·mL−1 with the limit of quantification (LOQ) of 1.7 mg·kg−1 for lutein in Marigold flowers and 200 mg·kg−1 in food supplements. Repeatability was 2.3 % for lutein in all tested matrices.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"12 - 6"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46429874","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract In this work, the possibility of flow coulometry application as coulometric titration was studied. The method was used to analyze phosphates in wastewater samples. The principle of the determination consisted in the formation of molybdophosphate and its subsequent one-electron electrolytic reduction. The present method is applicable under optimal conditions in the concentration range of 1.5 × 10−6 to 5.5 × 10−5 mol/dm3. Detection limit of the method is 3.42 × 10−7 mol/dm3. Mineralization step has been proved a problem in total phosphate content determination. If mineralization was not carried out, only inorganic soluble phosphates were determined. It is a new method characterized by its simplicity of instrumentation and handling, which is a prerequisite for its further use in the field of trace analysis.
{"title":"Determination of phosphate in water by flow coulometry","authors":"A. Manová, E. Beinrohr","doi":"10.2478/acs-2020-0015","DOIUrl":"https://doi.org/10.2478/acs-2020-0015","url":null,"abstract":"Abstract In this work, the possibility of flow coulometry application as coulometric titration was studied. The method was used to analyze phosphates in wastewater samples. The principle of the determination consisted in the formation of molybdophosphate and its subsequent one-electron electrolytic reduction. The present method is applicable under optimal conditions in the concentration range of 1.5 × 10−6 to 5.5 × 10−5 mol/dm3. Detection limit of the method is 3.42 × 10−7 mol/dm3. Mineralization step has been proved a problem in total phosphate content determination. If mineralization was not carried out, only inorganic soluble phosphates were determined. It is a new method characterized by its simplicity of instrumentation and handling, which is a prerequisite for its further use in the field of trace analysis.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"102 - 107"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47653409","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Michaela Skřížovská, Hana Věžníková, Petra Roupcová
Abstract This paper focuses on the assessment of the inclination to self-ignition of various types of wood chips according to the methodology of European standard EN 15188. The study also assesses the effect of heating temperatures on the composition and quantity of gaseous products of heating. Gases were analysed using an infrared spectrometer with Fourier transformation. From the measured results it was found that the inclination to self-ignition differs for various samples of wood chips. The paper discusses certain parameters assumed to affect the inclination of biomass to self-ignite. When assessing the effect of temperature on the composition of gaseous products, a sample of forest wood chips heated at temperatures from 50 to 150 °C resulted in the following gaseous products: carbon dioxide, carbon monoxide, water and aliphatic hydrocarbons; their concentrations increase with the increasing temperature. Carbon oxides have been proposed as indicators of the state of stored materials self-heating. Observations presented in this paper can be used as data for elaborating safety instructions for storage of fuels based on solid biomass.
{"title":"Inclination to self-ignition and analysis of gaseous products of wood chips heating","authors":"Michaela Skřížovská, Hana Věžníková, Petra Roupcová","doi":"10.2478/acs-2020-0013","DOIUrl":"https://doi.org/10.2478/acs-2020-0013","url":null,"abstract":"Abstract This paper focuses on the assessment of the inclination to self-ignition of various types of wood chips according to the methodology of European standard EN 15188. The study also assesses the effect of heating temperatures on the composition and quantity of gaseous products of heating. Gases were analysed using an infrared spectrometer with Fourier transformation. From the measured results it was found that the inclination to self-ignition differs for various samples of wood chips. The paper discusses certain parameters assumed to affect the inclination of biomass to self-ignite. When assessing the effect of temperature on the composition of gaseous products, a sample of forest wood chips heated at temperatures from 50 to 150 °C resulted in the following gaseous products: carbon dioxide, carbon monoxide, water and aliphatic hydrocarbons; their concentrations increase with the increasing temperature. Carbon oxides have been proposed as indicators of the state of stored materials self-heating. Observations presented in this paper can be used as data for elaborating safety instructions for storage of fuels based on solid biomass.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"88 - 97"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45219690","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Petra Roupcová, K. Klouda, P. Brandeburová, R. Šípoš, J. Híveš, M. Gál, T. Mackuľak, Michaela Skřížovská, Lenka Kissiková
Abstract Research on carbon-based nanomaterials (CBNMs) and their development is one of the major scientific disciplines of the last century. This is mainly because of their unique properties which can lead to improvements in industrial technology or new medical applications. Therefore, it is necessary to examine their properties such as shape, size, chemical composition, density, toxicity, etc. This article focuses on the general characteristics of nanomaterials (NMs) and their behavior when entering the environment (water and soil). In addition, it presents individual members of the graphene family including porous ecological carbon (biochar). The article mainly deals with the new potential technologies of CBNMs considering their possible toxic and genotoxic effects. This review also highlights the latest developments in the application of self-propelled micromotors for green chemistry applications. Finally, it points to the potential biomedical applications of CBNMs.
{"title":"Carbon family nanomaterials — new applications and technologies","authors":"Petra Roupcová, K. Klouda, P. Brandeburová, R. Šípoš, J. Híveš, M. Gál, T. Mackuľak, Michaela Skřížovská, Lenka Kissiková","doi":"10.2478/acs-2020-0012","DOIUrl":"https://doi.org/10.2478/acs-2020-0012","url":null,"abstract":"Abstract Research on carbon-based nanomaterials (CBNMs) and their development is one of the major scientific disciplines of the last century. This is mainly because of their unique properties which can lead to improvements in industrial technology or new medical applications. Therefore, it is necessary to examine their properties such as shape, size, chemical composition, density, toxicity, etc. This article focuses on the general characteristics of nanomaterials (NMs) and their behavior when entering the environment (water and soil). In addition, it presents individual members of the graphene family including porous ecological carbon (biochar). The article mainly deals with the new potential technologies of CBNMs considering their possible toxic and genotoxic effects. This review also highlights the latest developments in the application of self-propelled micromotors for green chemistry applications. Finally, it points to the potential biomedical applications of CBNMs.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"77 - 87"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44600820","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract Berberine (1), as a compound with interesting biological activities, can be modified at various positions to obtain more potent substances. Modifications at position 9 are based on demethylation with simultaneous dechloration resulting in berberrubine. The most frequent process is thermal dechloromethylation and this work describes this method with detailed tricks to obtain almost pure product in high yield.
{"title":"Dechloromethylation of the berberine to berberrubine — tricks to obtain pure product","authors":"V. Milata, Eva Holúbková","doi":"10.2478/acs-2020-0014","DOIUrl":"https://doi.org/10.2478/acs-2020-0014","url":null,"abstract":"Abstract Berberine (1), as a compound with interesting biological activities, can be modified at various positions to obtain more potent substances. Modifications at position 9 are based on demethylation with simultaneous dechloration resulting in berberrubine. The most frequent process is thermal dechloromethylation and this work describes this method with detailed tricks to obtain almost pure product in high yield.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"101 - 98"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41549518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract Coumarins (2H-1-benzopyran-2-coumarin derivatives) are derivatives of cinnamic acid naturally occurring in many plants, fungi, and fruits. They are used as ingredients in cosmetics to enhance the aroma and other biological effects. In this work, cosmetic samples (deodorants) were treated by solid phase extraction prior to high performance liquid chromatography determination of coumarins. Traditional sorbent (C18) and selective polymer-based sorbents (laboratory prepared and commercial) were used for solid phase extraction. Recovery values were above 85 % (RSDs below 6 %) except for esculin, where the recovery was lower. Core-shell column of C18 type and gradient of mobile phase methanol—1 % acetic acid were used for high performance liquid chromatography analysis of extracts. Limits of quantitation were 0.5 µg mL−1 for coumarin (ultraviolet detection) and below 12 ng mL−1 for esculin, umbelliferonene, scoparone, 4-methylumbelliferone, herniarin (fluorescence detection). In the tested samples, no coumarins were detected.
摘要香豆素（2H-1-苯并吡喃-2-香豆素衍生物）是肉桂酸的衍生物，天然存在于许多植物、真菌和水果中。它们被用作化妆品中的成分，以增强香气和其他生物效应。在这项工作中，在高效液相色谱法测定香豆素之前，通过固相萃取处理化妆品样品（除臭剂）。传统吸附剂（C18）和选择性聚合物基吸附剂（实验室制备和商业化）用于固相萃取。回收率高于85%（RSD低于6%），但埃斯库林的回收率较低。采用C18型核壳柱，流动相甲醇-1%乙酸梯度洗脱，对提取物进行高效液相色谱分析。香豆素（紫外检测）的定量限为0.5µg mL−1，而esculin、伞形花烯、东莨菪碱、4-甲基伞形花烯和疝环素（荧光检测）的含量限低于12 ng mL−1。在测试样品中，未检测到香豆素。
{"title":"Application of selective polymeric sorbents for simple coumarins extraction from deodorant samples","authors":"K. Hroboňová, Andrea Špačková","doi":"10.2478/acs-2020-0009","DOIUrl":"https://doi.org/10.2478/acs-2020-0009","url":null,"abstract":"Abstract Coumarins (2H-1-benzopyran-2-coumarin derivatives) are derivatives of cinnamic acid naturally occurring in many plants, fungi, and fruits. They are used as ingredients in cosmetics to enhance the aroma and other biological effects. In this work, cosmetic samples (deodorants) were treated by solid phase extraction prior to high performance liquid chromatography determination of coumarins. Traditional sorbent (C18) and selective polymer-based sorbents (laboratory prepared and commercial) were used for solid phase extraction. Recovery values were above 85 % (RSDs below 6 %) except for esculin, where the recovery was lower. Core-shell column of C18 type and gradient of mobile phase methanol—1 % acetic acid were used for high performance liquid chromatography analysis of extracts. Limits of quantitation were 0.5 µg mL−1 for coumarin (ultraviolet detection) and below 12 ng mL−1 for esculin, umbelliferonene, scoparone, 4-methylumbelliferone, herniarin (fluorescence detection). In the tested samples, no coumarins were detected.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"13 1","pages":"56 - 62"},"PeriodicalIF":0.8,"publicationDate":"2020-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43915443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract Due to the substantial protective effects of milk thistle to liver against various chemical compounds, a new healthy cereal product replacing wheat flour with milk thistle seed flour in the range of 5; 10; 15; 20; 25 and 30 % has been studied. As it has been found, milk thistle seed flour is a good source of total dietary fibre, proteins, mineral compounds and fats. During the experiments, effects of wheat flour replacement on technological properties of the dough were studied using Mixolab characteristics. From the results it can be stated that milk thistle seed flour replacement led to a decrease in water absorption and stability of dough. After baking, physical, mechanical, colour and sensorial properties of the biscuits were studied. The results have shown that even a 10 % replacement results in a significant difference at p < 0.05 in measured parameters compared to ones. However, it has been calculated that statistically insignificant replacement of wheat flour with milk thistle seed flour is up to 9.3 % with quality and sensorial parameters of the biscuits equal to those prepared from 100 % wheat flour. Thus, production of functional biscuits at these conditions is fully possible.
{"title":"Application of milk thistle (Silybum marianum) in functional biscuits formulation","authors":"Veronika Bortlíková, L. Kolarič, P. Šimko","doi":"10.2478/acs-2019-0027","DOIUrl":"https://doi.org/10.2478/acs-2019-0027","url":null,"abstract":"Abstract Due to the substantial protective effects of milk thistle to liver against various chemical compounds, a new healthy cereal product replacing wheat flour with milk thistle seed flour in the range of 5; 10; 15; 20; 25 and 30 % has been studied. As it has been found, milk thistle seed flour is a good source of total dietary fibre, proteins, mineral compounds and fats. During the experiments, effects of wheat flour replacement on technological properties of the dough were studied using Mixolab characteristics. From the results it can be stated that milk thistle seed flour replacement led to a decrease in water absorption and stability of dough. After baking, physical, mechanical, colour and sensorial properties of the biscuits were studied. The results have shown that even a 10 % replacement results in a significant difference at p < 0.05 in measured parameters compared to ones. However, it has been calculated that statistically insignificant replacement of wheat flour with milk thistle seed flour is up to 9.3 % with quality and sensorial parameters of the biscuits equal to those prepared from 100 % wheat flour. Thus, production of functional biscuits at these conditions is fully possible.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"12 1","pages":"192 - 199"},"PeriodicalIF":0.8,"publicationDate":"2019-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46441647","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract The topic of free radicals and related antioxidants is greatly discussed nowadays. Antioxidants help to neutralize free radicals before damaging cells. In the absence of antioxidants, a phenomenon called oxidative stress occurs. Oxidative stress can cause many diseases e.g. Alzheimer’s disease and cardiovascular diseases. Therefore, antioxidant activity of various compounds and the mechanism of their action have to be studied. Antioxidant activity and capacity are measured by in vitro and in vivo methods; in vitro methods are divided into two groups according to chemical reactions between free radicals and antioxidants. The first group is based on the transfer of hydrogen atoms (HAT), the second one on the transfer of electrons (ET). The most frequently used methods in the field of antioxidant power measurement are discussed in this work in terms of their principle, mechanism, methodology, the way of results evaluation and possible pitfalls.
{"title":"Selectedin vitro methods to determine antioxidant activity of hydrophilic/lipophilic substances","authors":"A. Ácsová, Silvia Martiniaková, J. Hojerová","doi":"10.2478/acs-2019-0028","DOIUrl":"https://doi.org/10.2478/acs-2019-0028","url":null,"abstract":"Abstract The topic of free radicals and related antioxidants is greatly discussed nowadays. Antioxidants help to neutralize free radicals before damaging cells. In the absence of antioxidants, a phenomenon called oxidative stress occurs. Oxidative stress can cause many diseases e.g. Alzheimer’s disease and cardiovascular diseases. Therefore, antioxidant activity of various compounds and the mechanism of their action have to be studied. Antioxidant activity and capacity are measured by in vitro and in vivo methods; in vitro methods are divided into two groups according to chemical reactions between free radicals and antioxidants. The first group is based on the transfer of hydrogen atoms (HAT), the second one on the transfer of electrons (ET). The most frequently used methods in the field of antioxidant power measurement are discussed in this work in terms of their principle, mechanism, methodology, the way of results evaluation and possible pitfalls.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"12 1","pages":"200 - 211"},"PeriodicalIF":0.8,"publicationDate":"2019-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42693136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hydroxymethyl group is present in many useful and biologically potent substances like sugars, kojic acid (Bajpai, 1982), ronicol (3-hydroxymethylpyridine) (Moncol, 2006; Broghammer, 1967) or hydroxymethylphenol — intermediate for bakelite (Baekeland, 1909). On the other hand, 4-quinolones are a group of antibacterials with various biological activities if substituted in position 3and they are anti-CNS and similar diseases agents if substituted in position 2(kynurenic acid derivatives) (Turski, 2013; Szalardy, 2012; Fulop, 2009). Considering this, we were interested in the synthesis of 3-hydroxymethyl-1,4dihydro-4-oxoquinoline. 4-Quinolones are a well-known group of chemotherapeutics with a broad spectrum of activities (Andriole, 2000; Milata, 2000) based on inhibition of the enzyme of bacterial topoisomerase II (DNA gyrase) and topoisomerase IV in Gram-positive species, thus inhibiting tertiary negative supercoiling of bacterial DNA (Gellert, 1976; Wang, 1985; Gootz, 1996) mostly bound to oxygen atoms in positions 3and 4of the fused pyrid-4-one-3-carboxylic acid moiety (Andriole, 2000). Therefore, it should be interesting to prepare and evaluate the corresponding structural motif, namely 3-hydroxymethylquinol4-one. Substructural search in database SciFinder provided only various applications of formaldehyde with 4-quinolones or their precursors (Goldsworthy, 1982) but no true synthesis has been reported. Therefore, this compound with promising binding and complexing activity has been prepared.
{"title":"3-Hydroxymethyl-1,4-dihydro-4-oxoquinoline like compound with promising biological and complexing activity","authors":"V. Milata, Maroš Bella, Robert Kurinec","doi":"10.2478/acs-2019-0025","DOIUrl":"https://doi.org/10.2478/acs-2019-0025","url":null,"abstract":"Hydroxymethyl group is present in many useful and biologically potent substances like sugars, kojic acid (Bajpai, 1982), ronicol (3-hydroxymethylpyridine) (Moncol, 2006; Broghammer, 1967) or hydroxymethylphenol — intermediate for bakelite (Baekeland, 1909). On the other hand, 4-quinolones are a group of antibacterials with various biological activities if substituted in position 3and they are anti-CNS and similar diseases agents if substituted in position 2(kynurenic acid derivatives) (Turski, 2013; Szalardy, 2012; Fulop, 2009). Considering this, we were interested in the synthesis of 3-hydroxymethyl-1,4dihydro-4-oxoquinoline. 4-Quinolones are a well-known group of chemotherapeutics with a broad spectrum of activities (Andriole, 2000; Milata, 2000) based on inhibition of the enzyme of bacterial topoisomerase II (DNA gyrase) and topoisomerase IV in Gram-positive species, thus inhibiting tertiary negative supercoiling of bacterial DNA (Gellert, 1976; Wang, 1985; Gootz, 1996) mostly bound to oxygen atoms in positions 3and 4of the fused pyrid-4-one-3-carboxylic acid moiety (Andriole, 2000). Therefore, it should be interesting to prepare and evaluate the corresponding structural motif, namely 3-hydroxymethylquinol4-one. Substructural search in database SciFinder provided only various applications of formaldehyde with 4-quinolones or their precursors (Goldsworthy, 1982) but no true synthesis has been reported. Therefore, this compound with promising binding and complexing activity has been prepared.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"12 1","pages":"182 - 184"},"PeriodicalIF":0.8,"publicationDate":"2019-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47506151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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