Pub Date : 2023-05-11DOI: 10.20450/mjcce.2023.2554
P. Koparir
4-(((4-Ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)thio)methyl)-7-methyl-coumarin was synthesized, and its characterization was done with quantum chemical calculations and spectral techniques. The density functional method (B3LYP) with the 6-311G(d,p) basis set was used to calculate the molecular geometry, vibrational frequencies, and gauge, including atomic orbital (GIAO) 1H and 13C-NMR chemical shift values of the title compound in the ground state. The theoretical vibrational frequencies and chemical shift values agree well with the experimental results. DFT calculations of the density of states (DOS) and frontier molecular orbitals of the title compound were carried out at the B3LYP/6-311G(d,p) level of theory. In the present study, biological activities and molecular docking studies of this triazole ring containing coumarin derivative compound were carried out. Interactions with important residues in active sites were detected in molecular docking studies. In addition, in vitro analysis has shown that anti-microorganism activity is especially effective against bacterial organisms such as E. coli, S. aureus, B. cereus, and fungal organisms such as C. albicans, C. tropicalis. Also, the antioxidant capacity of the test compound was investigated by oxidative stress index (OSI) and radical scavenging power (DPPH.), and its antioxidant potential was found. In addition, it was determined by in vitro anticancer and SDS-PAGE analysis that the test compound does not cause a detrimental cytotoxic effect on healthy cell cultures such as HUVEC and has the potential for anticarcinogenic activity on MCF-7 and MKN-45 cancerous cell cultures.
{"title":"Bioactivity and quantum chemical calculations оf a new coumarine derivative as a strong antioxidant, antimicrobial and anti-cancer substance","authors":"P. Koparir","doi":"10.20450/mjcce.2023.2554","DOIUrl":"https://doi.org/10.20450/mjcce.2023.2554","url":null,"abstract":"4-(((4-Ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)thio)methyl)-7-methyl-coumarin was synthesized, and its characterization was done with quantum chemical calculations and spectral techniques. The density functional method (B3LYP) with the 6-311G(d,p) basis set was used to calculate the molecular geometry, vibrational frequencies, and gauge, including atomic orbital (GIAO) 1H and 13C-NMR chemical shift values of the title compound in the ground state. The theoretical vibrational frequencies and chemical shift values agree well with the experimental results. DFT calculations of the density of states (DOS) and frontier molecular orbitals of the title compound were carried out at the B3LYP/6-311G(d,p) level of theory. In the present study, biological activities and molecular docking studies of this triazole ring containing coumarin derivative compound were carried out. Interactions with important residues in active sites were detected in molecular docking studies. In addition, in vitro analysis has shown that anti-microorganism activity is especially effective against bacterial organisms such as E. coli, S. aureus, B. cereus, and fungal organisms such as C. albicans, C. tropicalis. Also, the antioxidant capacity of the test compound was investigated by oxidative stress index (OSI) and radical scavenging power (DPPH.), and its antioxidant potential was found. In addition, it was determined by in vitro anticancer and SDS-PAGE analysis that the test compound does not cause a detrimental cytotoxic effect on healthy cell cultures such as HUVEC and has the potential for anticarcinogenic activity on MCF-7 and MKN-45 cancerous cell cultures.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2023-05-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49453111","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-04-28DOI: 10.20450/mjcce.2023.2589
Öznur Doğan Ulu
In this study, a 1,3-dioxane functionalized benzimidazole salt and its Ag-complex were synthe-sized. The prepared compounds were structurally verified by several spectroscopic techniques including 1H NMR, 13C NMR, FT-IR, LC-MS, and C, H, N analysis. Compounds were evaluated for their in vitro antioxidant activity. The salts and their Ag-NHC complexes were further evaluated for their in vitro anti-cancer activities against HCT-116 human colon cancer cells. The results showed that complex 2 exhibited high activity (4.1 times) against the cancer cell lines studied when compared to the reference drug cispla-tin. Stability studies demonstrated that these compounds are stable in aqueous and organic solutions.
{"title":"Synthesis, characterization, and biological activity of 1,3-disubstitued benzimidazolium salt and its Ag-NHC complex","authors":"Öznur Doğan Ulu","doi":"10.20450/mjcce.2023.2589","DOIUrl":"https://doi.org/10.20450/mjcce.2023.2589","url":null,"abstract":"In this study, a 1,3-dioxane functionalized benzimidazole salt and its Ag-complex were synthe-sized. The prepared compounds were structurally verified by several spectroscopic techniques including 1H NMR, 13C NMR, FT-IR, LC-MS, and C, H, N analysis. Compounds were evaluated for their in vitro antioxidant activity. The salts and their Ag-NHC complexes were further evaluated for their in vitro anti-cancer activities against HCT-116 human colon cancer cells. The results showed that complex 2 exhibited high activity (4.1 times) against the cancer cell lines studied when compared to the reference drug cispla-tin. Stability studies demonstrated that these compounds are stable in aqueous and organic solutions.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2023-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47998297","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-31DOI: 10.20450/mjcce.2022.2585
F. Arslan, Hasan Koçak, O. Bodur, E. Hasanoğlu Özkan, B. Arslan, N. Sarı
A novel biosensor for the determination of Bisphenol-A has been developed in this study. For this purpose, a carbon paste electrode modified with poly(amidoamine)-salicylidenimine platinum(II) (PAMAM-Sal-Pt(II)) and the tyrosinase enzyme was prepared. BPA determination was based on the electrochemical reduction of an enzymatically produced quinone compound at –0.15 V. Optimum working conditions for the prepared biosensor were investigated. The linear working range and detection limit were found to be 0.01–1.0 μM and 1 nM, respectively. The optimum pH value and working temperature were defined as 7.0 and 40 ℃, respectively. The reproducibility of the biosensor is very good. It was found that phenol, nitrophenol, urea, potassium nitrate, hexane, acetonitrile, and ethyl acetate do not interfere with the BPA determination. The prepared biosensor was used for the first time in dentistry for the determination of BPA in a resin-based composite material used as a bracket adhesive in orthodontics.
{"title":"Novel tyrosinase-based bisphenol-A biosensor for the determination of bisphenol-A in bracket adhesive in orthodontics","authors":"F. Arslan, Hasan Koçak, O. Bodur, E. Hasanoğlu Özkan, B. Arslan, N. Sarı","doi":"10.20450/mjcce.2022.2585","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2585","url":null,"abstract":"A novel biosensor for the determination of Bisphenol-A has been developed in this study. For this purpose, a carbon paste electrode modified with poly(amidoamine)-salicylidenimine platinum(II) (PAMAM-Sal-Pt(II)) and the tyrosinase enzyme was prepared. BPA determination was based on the electrochemical reduction of an enzymatically produced quinone compound at –0.15 V. Optimum working conditions for the prepared biosensor were investigated. The linear working range and detection limit were found to be 0.01–1.0 μM and 1 nM, respectively. The optimum pH value and working temperature were defined as 7.0 and 40 ℃, respectively. The reproducibility of the biosensor is very good. It was found that phenol, nitrophenol, urea, potassium nitrate, hexane, acetonitrile, and ethyl acetate do not interfere with the BPA determination. The prepared biosensor was used for the first time in dentistry for the determination of BPA in a resin-based composite material used as a bracket adhesive in orthodontics.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44445008","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-31DOI: 10.20450/mjcce.2022.2633
Владимир Петрушевски
Бев поканет и го прифатив предизвикот, по што се обидов да го преведам/препеам текстот од хумористичниот Периоден систем на елементите, даден на англиски јазик1. При ова си поставив неколку императиви од самиот почеток: 1) Текстот на секоја слика да биде во стихови (најдобро дистих или скриен дистих), при што двата стиха да бидат со еднаква стапка. 2) Предност да имаат римувани стихови (секаде каде што тоа е возможно). 3) Кога тоа може да се стори, да не се отстапува од оригиналот во однос на клучните зборови/поими (последново се покажа како речиси невозможна мисија, па отстапено е во определен број случаи, нудејќи решенија што се во непосредна врска со својствата на дадениот елемент, а држејќи се до императивите 1) и 2). 4) Во еден мал број случаи (в. го четвртиот пример во овој труд) препевот е даден со моностихови, ценејќи дека со непотребно инсистирање врз римата и стапката би се изгубила „пораката“ од оригиналот. Даден е (споредбено/табеларно) англискиот оригинал и препевот на текстот за десетина елементи, со кратки коментари. Таму каде што постои позначително отстапување на текстот од оригиналот е коментирано и која била мотивацијата за таквото решение.
{"title":"Превод/препев на хумористичниот Периоден систем на македонски","authors":"Владимир Петрушевски","doi":"10.20450/mjcce.2022.2633","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2633","url":null,"abstract":"Бев поканет и го прифатив предизвикот, по што се обидов да го преведам/препеам текстот од хумористичниот Периоден систем на елементите, даден на англиски јазик1. При ова си поставив неколку императиви од самиот почеток: 1) Текстот на секоја слика да биде во стихови (најдобро дистих или скриен дистих), при што двата стиха да бидат со еднаква стапка. 2) Предност да имаат римувани стихови (секаде каде што тоа е возможно). 3) Кога тоа може да се стори, да не се отстапува од оригиналот во однос на клучните зборови/поими (последново се покажа како речиси невозможна мисија, па отстапено е во определен број случаи, нудејќи решенија што се во непосредна врска со својствата на дадениот елемент, а држејќи се до императивите 1) и 2). 4) Во еден мал број случаи (в. го четвртиот пример во овој труд) препевот е даден со моностихови, ценејќи дека со непотребно инсистирање врз римата и стапката би се изгубила „пораката“ од оригиналот.\u0000Даден е (споредбено/табеларно) англискиот оригинал и препевот на текстот за десетина елементи, со кратки коментари. Таму каде што постои позначително отстапување на текстот од оригиналот е коментирано и која била мотивацијата за таквото решение.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43307839","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-31DOI: 10.20450/mjcce.2022.2579
N. Genc
Nanoparticles have attracted great interest recently due to their application in many fields. In this study, an eco-friendly, scalable, cost-effective method was used for the synthesis of silver nanoparticles (s-AgNPs) using the fruit extract of Sphaerophysa kotschyana as a reducing agent, and their structure was elucidated by extensive spectroscopic techniques. The color change from yellow to dark brown indicated the formation of s-AgNPs. In the UV-Vis spectrum, the maximum absorption was observed at 437 nm. Fourier transform infrared (FTIR) spectroscopy displayed the functional group of the natural compounds in the extract that capped and stabilized the s-AgNPs. The characteristic hydroxyl vibrational signal appeared at 3168 cm–1. The X-ray diffraction (XRD) pattern indicated that the s-AgNPs were face-centered cubic crystalline structures. Scanning electron microscopy (SEM) exhibited the spherical-shaped nanoparticles with an average size of 67.37 nm. The antioxidant activity of the extract and s-AgNPs was established using the DPPH, ABTS, and FRAP assays. In the DPPH test, the effect of s-AgNPs was observed to be significantly higher than that of the extract, and the activity of s-AgNPs in the FRAP test was also reported to be higher than the extract. In the ABTS assay, the s-AgNPs displayed outstanding activity, which was even better than the standards. Consequently, s-AgNPs synthesized from S. kotschyana are promising drug products for diseases caused by oxidative stress.
{"title":"Synthesis and characterization of silver nanoparticles using Sphaerophysa kotschyana fruit and the assessment of their antioxidant activity","authors":"N. Genc","doi":"10.20450/mjcce.2022.2579","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2579","url":null,"abstract":"Nanoparticles have attracted great interest recently due to their application in many fields. In this study, an eco-friendly, scalable, cost-effective method was used for the synthesis of silver nanoparticles (s-AgNPs) using the fruit extract of Sphaerophysa kotschyana as a reducing agent, and their structure was elucidated by extensive spectroscopic techniques. The color change from yellow to dark brown indicated the formation of s-AgNPs. In the UV-Vis spectrum, the maximum absorption was observed at 437 nm. Fourier transform infrared (FTIR) spectroscopy displayed the functional group of the natural compounds in the extract that capped and stabilized the s-AgNPs. The characteristic hydroxyl vibrational signal appeared at 3168 cm–1. The X-ray diffraction (XRD) pattern indicated that the s-AgNPs were face-centered cubic crystalline structures. Scanning electron microscopy (SEM) exhibited the spherical-shaped nanoparticles with an average size of 67.37 nm. The antioxidant activity of the extract and s-AgNPs was established using the DPPH, ABTS, and FRAP assays. In the DPPH test, the effect of s-AgNPs was observed to be significantly higher than that of the extract, and the activity of s-AgNPs in the FRAP test was also reported to be higher than the extract. In the ABTS assay, the s-AgNPs displayed outstanding activity, which was even better than the standards. Consequently, s-AgNPs synthesized from S. kotschyana are promising drug products for diseases caused by oxidative stress.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42131883","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-30DOI: 10.20450/mjcce.2022.2565
Sara Kurdo Kamal, Yavuz Yardım
In this study, the electrochemical determination of the amodiaquine (ADQ) drug was evaluated using an electrochemically pretreated boron-doped diamond (BDD) electrode due to the enhanced surface activity. The cyclic voltammogram results of ADQ were given as single reversible and diffusion-controlled peaks at +0.48 V for the oxidation peak and +0.05 V for the reduction peak (vs. Ag/AgCl) in Britton-Robinson (BR) buffer at pH 8.0. The peak potential and current signals of ADQ were evaluated at the surface of the BDD electrode using instrumental parameters to develop a simple method for ADQ detection. Also, the effect of an anionic surfactant, sodium dodecyl sulfate (SDS), on the adsorption applicability of the BDD electrode significantly increased the stripping voltammetric determination of ADQ. Under the optimal conditions chosen and employing square-wave adsorptive stripping voltammetry at the BDD electrode, ADQ was determined at + 0.34 V (vs. Ag/AgCl) at the open-circuit condition in BR buffer at pH 8.0 in the presence of 2·10–4 mol l–1 SDS. Furthermore, analytical parameters showed the linear relationship for ADQ determination in the concentration range of 0.1–20.0 μg ml–1 (2.2·10–7 – 4.3·10–5 mol l–1), with a detection limit of 0.03 μg ml–1 (6.5·10–8 mol l–1). The proposed approach can be applied to determine ADQ in water samples.
{"title":"Voltammetric determination of anti-malarial drug amodiaquine at a boron-doped diamond electrode surface in an anionic surfactant media","authors":"Sara Kurdo Kamal, Yavuz Yardım","doi":"10.20450/mjcce.2022.2565","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2565","url":null,"abstract":"In this study, the electrochemical determination of the amodiaquine (ADQ) drug was evaluated using an electrochemically pretreated boron-doped diamond (BDD) electrode due to the enhanced surface activity. The cyclic voltammogram results of ADQ were given as single reversible and diffusion-controlled peaks at +0.48 V for the oxidation peak and +0.05 V for the reduction peak (vs. Ag/AgCl) in Britton-Robinson (BR) buffer at pH 8.0. The peak potential and current signals of ADQ were evaluated at the surface of the BDD electrode using instrumental parameters to develop a simple method for ADQ detection. Also, the effect of an anionic surfactant, sodium dodecyl sulfate (SDS), on the adsorption applicability of the BDD electrode significantly increased the stripping voltammetric determination of ADQ. Under the optimal conditions chosen and employing square-wave adsorptive stripping voltammetry at the BDD electrode, ADQ was determined at + 0.34 V (vs. Ag/AgCl) at the open-circuit condition in BR buffer at pH 8.0 in the presence of 2·10–4 mol l–1 SDS. Furthermore, analytical parameters showed the linear relationship for ADQ determination in the concentration range of 0.1–20.0 μg ml–1 (2.2·10–7 – 4.3·10–5 mol l–1), with a detection limit of 0.03 μg ml–1 (6.5·10–8 mol l–1). The proposed approach can be applied to determine ADQ in water samples.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47012804","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-30DOI: 10.20450/mjcce.2022.2494
E. Mateev, M. Georgieva, A. Zlatkov
In this study, one novel N-pyrrolyl carboxylic acid (3), the corresponding N-pyrrolyl hydrazide (5), and four new hydrazide-hydrazones (5a-d) bearing electron donating moieties were designed, synthesized, and fully elucidated by 1H NMR, FT-IR, and HRMS. The hydrazide-hydrazones were produced in five steps, which were optimized by applying microwave heating. The microwave-assisted synthesis significantly decreased the reaction times and increased the yields of the title molecules. In addition, all novel compounds were assessed for their radical scavenging properties by employing DPPH and ABTS assays. The most promising agent was obtained after condensation of the title hydrazide (5) with a 3,5-dimetoxy-4-hydroxybenzaldehyde (5d). The latter compound showed better antioxidant properties than Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and could serve as a prominent lead structure for future optimization as an antioxidant agent. A possible binding conformation of 5d in the active site of NADPH oxidase was also identified through molecular docking simulations. Analysis of the major interactions showed the importance of the hydroxyl moiety for the antioxidant activity. Finally, the virtual calculations of the ADME properties of the synthesized compounds displayed good drug-like properties. Overall, an optimized synthetic protocol through MW irradiation was employed. The newly synthesized ethyl (E)-5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazineyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (5d) was found to possess the most prominent radical-scavenging capacity, which identifies it as a promising lead compound for the development of novel antioxidants.
{"title":"Design, microwave-assisted synthesis, biological evaluation, molecular docking and ADME studies of pyrrole-based hydrazide-hydrazones as potential antioxidant agents","authors":"E. Mateev, M. Georgieva, A. Zlatkov","doi":"10.20450/mjcce.2022.2494","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2494","url":null,"abstract":"In this study, one novel N-pyrrolyl carboxylic acid (3), the corresponding N-pyrrolyl hydrazide (5), and four new hydrazide-hydrazones (5a-d) bearing electron donating moieties were designed, synthesized, and fully elucidated by 1H NMR, FT-IR, and HRMS. The hydrazide-hydrazones were produced in five steps, which were optimized by applying microwave heating. The microwave-assisted synthesis significantly decreased the reaction times and increased the yields of the title molecules. In addition, all novel compounds were assessed for their radical scavenging properties by employing DPPH and ABTS assays. The most promising agent was obtained after condensation of the title hydrazide (5) with a 3,5-dimetoxy-4-hydroxybenzaldehyde (5d). The latter compound showed better antioxidant properties than Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and could serve as a prominent lead structure for future optimization as an antioxidant agent. A possible binding conformation of 5d in the active site of NADPH oxidase was also identified through molecular docking simulations. Analysis of the major interactions showed the importance of the hydroxyl moiety for the antioxidant activity. Finally, the virtual calculations of the ADME properties of the synthesized compounds displayed good drug-like properties. Overall, an optimized synthetic protocol through MW irradiation was employed. The newly synthesized ethyl (E)-5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazineyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (5d) was found to possess the most prominent radical-scavenging capacity, which identifies it as a promising lead compound for the development of novel antioxidants.","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44715153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-30DOI: 10.20450/mjcce.2022.2471
N. Uludağ
A new synthetic procedure has been developed to prepare the biologically important azocino[4,3-b]indole via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tetrahydrocarbazole derivative bearing an amide side chain at the C-2 position. For the first time, this strategy is based on a different method for the C-2 position of the tetrahydrocarbazole for the synthesis of methanoazocino[4,3-b]indole. The notable features of this protocol include its operational simplicity and high reaction yields. Furthermore, the structures of all the presently synthesized compounds were confirmed using spectroscopic methods (1H NMR, 13C NMR, FT-IR).
{"title":"A simple and efficient method for constructing azocino[4,3-b]indole","authors":"N. Uludağ","doi":"10.20450/mjcce.2022.2471","DOIUrl":"https://doi.org/10.20450/mjcce.2022.2471","url":null,"abstract":"A new synthetic procedure has been developed to prepare the biologically important azocino[4,3-b]indole via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tetrahydrocarbazole derivative bearing an amide side chain at the C-2 position. For the first time, this strategy is based on a different method for the C-2 position of the tetrahydrocarbazole for the synthesis of methanoazocino[4,3-b]indole. The notable features of this protocol include its operational simplicity and high reaction yields. Furthermore, the structures of all the presently synthesized compounds were confirmed using spectroscopic methods (1H NMR, 13C NMR, FT-IR).","PeriodicalId":18088,"journal":{"name":"Macedonian Journal of Chemistry and Chemical Engineering","volume":" ","pages":""},"PeriodicalIF":1.0,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47773619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-30DOI: 10.20450/mjcce.2022.2571
D. D. Thiaré, P. A. Diaw, O. Mbaye, Diégane Sarr, M. D. Gaye-Seye, S. Ruellan, P. Giamarchi, F. Delattre, A. Coly, J. Aaron
The photolysis of fenvalerate, a pyrethroid insecticide, was studied in acetonitrile by 1H nuclear magnetic resonance (NMR) and 13C NMR to identify the site of bond cleavage and gas chromatography-mass spectrometry (GC-MS) to establish the chemical structure of fenvalerate photoproducts. Ultraviolet (UV) irradiation of fenvalerate solutions was performed for 18 h with a solar light simulator, and the photolysis reaction obeyed first-order kinetics. Photolysis half-life time (t1/2) values ranged between 15.25 and 21.63 h (mean photodegradation percentage = 51.7 %) for 1H NMR and between 4.55 and 8.06 h (mean photodegradation percentage > 80 %) for 13C NMR. We observed five sites of bond cleavage, namely carbonyl-tertiary carbon, tertiary carbon-tertiary carbon, carbonyl-oxygen, carboxyl-tertiary carbon, and aromatic carbon-tertiary carbon, yielding photoproducts formation. GC-MS was associated with 1H NMR and 13C NMR to obtain a complete photodegradation mechanism. Before UV irradiation, two chromatogram peaks were obtained, due to the two fenvalerate isomers. Under irradiation, both peaks decreased, and new peaks appeared, corresponding to photoproduct formation. After a 12- to 13-h irradiation, 99.39 % of fenvalerate was degraded with a mean rate constant of 0.305 h–1. The chemical structure of the formed photoproducts was identified, either by using the National Institute of Standards and Technology (NIST) mass spectral database or by interpreting the mass spectra. Finally, a detailed mechanism was proposed for fenvalerate photodegradation.
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Pub Date : 2022-12-30DOI: 10.20450/mjcce.2022.2482
M. Kırıcı, M. Kırıcı, M. R. Taysı, U. Ispir
The aim of this study was to investigate the response of different doses of lipopolysaccharide (LPS) and extracellular product (ECP) antigens (25, 50, 100, 250, and 500 µg) obtained from Flavobacterium psychrophilum to changes in oxidative stress parameters (catalase [CAT], superoxide dismutase [SOD], glutathione peroxidase [GPx], glucose 6-phosphate dehydrogenase [G6PD], glutathione reductase [GR], and malondialdehyde [MDA]) in juvenile rainbow trout. For this purpose, 6 different doses of F. psychrophilum (102–106) were applied to the fish, and the lethal dose 50 % (LD50) value was determined as 1.33·104. Changes in MDA levels and antioxidant enzymes were determined by applying 25 % of the LD50 value to fish for 14 days. Accordingly, while F. psychrophilum increased GR, G6PD, GPx, and SOD activity, it decreased MDA levels and CAT activity. Initially, 25, 50, 100, 250, and 500 µg doses of ECP and LPS were applied to the fish; after 21 days, a 25 % dose of LD50 was applied to these fish. Fourteen days later, the fish were taken, and the changes in MDA levels and antioxidant enzymes were examined. As a result, it was determined that while ECP and LPS application decreased GR, G6PD, GPx, and SOD activity, there was an increase in MDA levels and CAT activity.
本研究旨在研究不同剂量嗜冷黄杆菌脂多糖(LPS)和细胞外产物(ECP)抗原(25、50、100、250和500µg)对虹鳟鱼幼鱼氧化应激参数(过氧化氢酶[CAT]、超氧化物歧化酶[SOD]、谷胱甘肽过氧化物酶[GPx]、葡萄糖6-磷酸脱氢酶[G6PD]、谷胱甘肽还原酶[GR]和丙二醛[MDA])变化的影响。为此，采用6种不同剂量(102 ~ 106)的嗜冷F. F. philrophilum，测定致死剂量50% (LD50)值为1.33·104。将25%的LD50值施用于鱼14天，测定MDA水平和抗氧化酶的变化。因此，在提高GR、G6PD、GPx和SOD活性的同时，降低了MDA水平和CAT活性。最初，分别给鱼施用25、50、100、250和500µg剂量的ECP和LPS;21天后，将25%的LD50施用于这些鱼。14天后，取鱼，检测MDA水平和抗氧化酶的变化。结果表明，虽然施用ECP和LPS降低了GR、G6PD、GPx和SOD活性，但增加了MDA水平和CAT活性。
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