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Russian Journal of Organic Chemistry最新文献

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Synthesis of New Indole-Containing Benzo[f]coumarin Derivatives and Their Effect on the Proliferation and Redox State of Rat C6 Glioma Cells 含吲哚的苯并[f]香豆素新衍生物的合成及其对大鼠 C6 胶质瘤细胞增殖和氧化还原状态的影响
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060034
T. A. Kulahava, V. A. Shumski, I. V. Mineyeva
{"title":"Synthesis of New Indole-Containing Benzo[f]coumarin Derivatives and Their Effect on the Proliferation and Redox State of Rat C6 Glioma Cells","authors":"T. A. Kulahava,&nbsp;V. A. Shumski,&nbsp;I. V. Mineyeva","doi":"10.1134/S1070428024060034","DOIUrl":"10.1134/S1070428024060034","url":null,"abstract":"<p>Modification of 2-acetyl-3<i>H</i>-benzo[<i>f</i>]chromen-3-one and 2-[(2<i>E</i>)-3-phenylprop-2-enoyl]-3<i>H</i>-benzo[<i>f</i>]chromen-3-one has been performed for the first time via the reaction with indole. The resulting benzo­[<i>f</i>]coumarins have been found to exhibit antioxidant properties in model systems: they react with hydrogen peroxide and sodium hypochlorite and regulate redox state of rat C6 glioma cells, which is reflected in reduced concentration of intracellular hydrogen peroxide and increased level of reduced glutathione. The synthesized compounds in the presence of exogenous hydrogen peroxide exert a protective effect on the cells, acting as antioxidants and restoring the redox balance. 2-[3-(1<i>H</i>-Indol-3-yl)-3-phenylpropanoyl]-3<i>H</i>-benzo[<i>f</i>]khromen-3-one at a micromolar concentrations inhibited the rat C6 glioma cell proliferation by 25–35%.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"995 - 1005"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222310","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}
引用次数: 0
Nucleophilic Functionalization of Tropylium Salts with Heterocyclic Amines and Carboxylic Acid Amides and Hydrazides 羰基盐与杂环胺和羧酸酰胺及酰肼的亲核官能化作用
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060010
L. P. Yunnikova, O. V. Pshenitsyna
{"title":"Nucleophilic Functionalization of Tropylium Salts with Heterocyclic Amines and Carboxylic Acid Amides and Hydrazides","authors":"L. P. Yunnikova,&nbsp;O. V. Pshenitsyna","doi":"10.1134/S1070428024060010","DOIUrl":"10.1134/S1070428024060010","url":null,"abstract":"<p>The review summarizes literature data on new nucleophilic functionalization reactions of tropylium salts with heterocyclic amines and monocarboxylic acid amides and hydrazides over the past decade.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"971 - 983"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227505","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}
引用次数: 0
Defluorination and Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-dihydronaphthalene in the System Zn–DMF. Synthesis of Perfluoro-1-ethyl- and -1-methylnaphthalenes 全氟四氢萘、烷基四氢萘和 4-甲基-1,2-二氢萘在 Zn-DMF 体系中的脱氟及其他转化。全氟-1-乙基萘和-1-甲基萘的合成
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060058
V. R. Sinyakov, T. V. Mezhenkova, V. M. Karpov, Ya. V. Zonov
{"title":"Defluorination and Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-dihydronaphthalene in the System Zn–DMF. Synthesis of Perfluoro-1-ethyl- and -1-methylnaphthalenes","authors":"V. R. Sinyakov,&nbsp;T. V. Mezhenkova,&nbsp;V. M. Karpov,&nbsp;Ya. V. Zonov","doi":"10.1134/S1070428024060058","DOIUrl":"10.1134/S1070428024060058","url":null,"abstract":"<p>The reaction of perfluorotetralin with zinc in DMF, followed by treatment with water, gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2′-binaphthalene, and octafluoronaphthalene. Under similar conditions, perfluoro-1-ethyltetralin was converted into a mixture of 1,2,3,4,6,7-hexafluoro-5-(per­fluoro­ethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes, perfluoro-6-methyltetralin gave rise to 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene, and per­fluoro-1-methylnaphthalene was obtained from perfluoro-4-methyl-1,2-dihydronaphthalene. Perfluoro-1-ethyl­tetralin reacted with bromine-activated zinc in DMF to produce a mixture containing (perfluoro-4-ethylnaph­thalen-1-yl)zinc bromide which was converted to 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene by the action of water, while its reaction with CuCl<sub>2</sub> afforded perfluoro-4,4′-diethyl-1,1′-binaphthalene.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1013 - 1021"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227508","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}
引用次数: 0
Quaternization of Ethyl Pyridin-2-ylcarbamate with Phenacyl Bromides 吡啶-2-基氨基甲酸乙酯与苯乙酰溴的季铵化反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060204
D. A. Lomov
{"title":"Quaternization of Ethyl Pyridin-2-ylcarbamate with Phenacyl Bromides","authors":"D. A. Lomov","doi":"10.1134/S1070428024060204","DOIUrl":"10.1134/S1070428024060204","url":null,"abstract":"<p>The reaction of ethyl pyridine-2-ylcarbamate with phenacyl bromides in acetonitrile gave 2-aryl-1-(ethoxycarbonyl)-2-hydroxy-2-phenyl-2,3-dihydro-1<i>H</i>-imidazo[1,2-<i>a</i>]pyridine-4-ium bromides which were con­­verted into 2-arylimidazo[1,2-<i>a</i>]pyridines by heating in acetic anhydride, followed by treatment with potassium carbonate.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1145 - 1148"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227510","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}
引用次数: 0
Ruthenium-Catalyzed Regioselective C7–H Arylation of 2-(Het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with Aryl Halides 钌催化的 2-(Het)芳基[1,2,4]三唑并[1,5-a]嘧啶与芳基卤化物的区域选择性 C7-H 芳基化反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060095
K. E. Shepelenko, I. G. Gnatiuk, V. M. Chernyshev
{"title":"Ruthenium-Catalyzed Regioselective C7–H Arylation of 2-(Het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with Aryl Halides","authors":"K. E. Shepelenko,&nbsp;I. G. Gnatiuk,&nbsp;V. M. Chernyshev","doi":"10.1134/S1070428024060095","DOIUrl":"10.1134/S1070428024060095","url":null,"abstract":"<p>Unusual direction of the C–H arylation of 2-(het)aryl[1,2,4]triazolo[1,5-<i>a</i>]pyrimidines with (het)aryl halides under catalysis by ruthenium(II) complexes has been revealed. The reaction involved activation of the C<sup>7</sup>–H bond rather than the C<sup>α</sup>–H bond of the (het)aryl substituent at C<sup>2</sup> of the triazolopyrimidine core. The arylation of 2-substituted [1,2,4]triazolo[1,5-<i>a</i>]pyrimidines with (het)aryl bromides afforded a series of 7-(het)aryl derivatives in good yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1042 - 1050"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222313","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}
引用次数: 0
Ultrasound-Assisted Synthesis and DFT Studies of Novel Schiff Bases Derived from 3-Methyl-1,3-benzothiazol-2(3H)-one in an Ionic Liquid Medium 离子液体介质中 3-甲基-1,3-苯并噻唑-2(3H)-酮衍生的新型希夫碱的超声辅助合成和 DFT 研究
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060150
Y. Bouchebcheb, D. Fedaoui, A. Alem, M. Liacha
{"title":"Ultrasound-Assisted Synthesis and DFT Studies of Novel Schiff Bases Derived from 3-Methyl-1,3-benzothiazol-2(3H)-one in an Ionic Liquid Medium","authors":"Y. Bouchebcheb,&nbsp;D. Fedaoui,&nbsp;A. Alem,&nbsp;M. Liacha","doi":"10.1134/S1070428024060150","DOIUrl":"10.1134/S1070428024060150","url":null,"abstract":"<p>A new series of Schiff bases have been prepared by the condensation between 3-methyl-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde and primary aromatic amines using an eco-friendly method that employs the ionic liquid triethylammonium acetate [TEAA] as a solvent and catalyst at 80°C under ultrasonic irradiation. This protocol has a number of benefits, including short reaction times, direct isolation of the pure product, and high yield. The structures of the newly synthesized derivatives were established on the basis of IR, <sup>1</sup>H NMR, and <sup>13</sup>C NMR spectroscopic techniques (including two-dimensional <sup>1</sup>H–<sup>13</sup>C HSQC and <sup>1</sup>H–<sup>13</sup>C HMBC experiments) and elemental analysis. A DFT theoretical study was carried out for the synthesized molecules in the gas phase using the B3LYP method with 6-311G(<i>d</i>,<i>p</i>) basis set; the HUMO and LUMO energies were calculated for the optimized geometries, which showed that compound <b>4e</b> is the most stable with an energy gap of 4.05585 eV, as presented by the DOS spectrum. The reactivity of the compounds was studied by calculating some global reactivity descriptors, revealing that compound <b>4b</b> is the most chemically reactive. In addition, molecular electrostatic potentials (MEP) was studied for the reaction centers of the synthesized compounds.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1107 - 1116"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222332","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}
引用次数: 0
Expanding the Scope of Metal-Free Catalytic Approach for the Green One-Pot Multicomponent Synthesis of β-Amido Carbonyl Scaffolds 扩大无金属催化法在β-酰胺基羰基支架绿色一锅多组分合成中的应用范围
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060174
K. Ramya, Seena Chakko, V. S. Shinu, S. Arun
{"title":"Expanding the Scope of Metal-Free Catalytic Approach for the Green One-Pot Multicomponent Synthesis of β-Amido Carbonyl Scaffolds","authors":"K. Ramya,&nbsp;Seena Chakko,&nbsp;V. S. Shinu,&nbsp;S. Arun","doi":"10.1134/S1070428024060174","DOIUrl":"10.1134/S1070428024060174","url":null,"abstract":"<p>An efficient, mild, and green one-pot multicomponent synthetic approach has been proposed for the synthesis of β-amido carbonyl scaffolds via coupling of aromatic aldehydes, enolizable ketones, and acetonitrile in the presence of acetyl chloride and ammonium chloride as a metal-free highly effective catalyst. The developed approach provides a novel cost-effective and environmentally friendly route to access highly functionalized structural scaffolds in in good to excellent yields and requires less operational skill and conditions.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1123 - 1128"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222335","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}
引用次数: 0
Synthesis of Bi- and Polycyclic Pyrimidine Derivatives 双环和多环嘧啶衍生物的合成
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060046
T. V. Sokolnikova, A. G. Proidakov, M. V. Penzik, V. N. Kizhnyaev
{"title":"Synthesis of Bi- and Polycyclic Pyrimidine Derivatives","authors":"T. V. Sokolnikova,&nbsp;A. G. Proidakov,&nbsp;M. V. Penzik,&nbsp;V. N. Kizhnyaev","doi":"10.1134/S1070428024060046","DOIUrl":"10.1134/S1070428024060046","url":null,"abstract":"<p>Various bi- and polycyclic pyrimidine derivatives (including fused ones) containing different aza- and carbocyclic fragments have been synthesized via a modified Biginelli reaction.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1006 - 1012"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222309","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}
引用次数: 0
Intramolecular Heterocyclization of Quinolyl-Substituted Carbothioamides to Functionalized 2,4-Dihydro-3H-1,2,4-triazoles and -1,3,4-thiadiazoles 喹啉基取代的硫代碳酸酰胺分子内杂环化为功能化的 2,4- 二氢-3H-1,2,4-三唑和-1,3,4-噻二唑
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S107042802406006X
I. L. Aleksanyan, L. P. Hambardzumyan
{"title":"Intramolecular Heterocyclization of Quinolyl-Substituted Carbothioamides to Functionalized 2,4-Dihydro-3H-1,2,4-triazoles and -1,3,4-thiadiazoles","authors":"I. L. Aleksanyan,&nbsp;L. P. Hambardzumyan","doi":"10.1134/S107042802406006X","DOIUrl":"10.1134/S107042802406006X","url":null,"abstract":"<p>A simple and economical approach has been proposed for the transformation of 2-(quinolyl­propanoyl)-<i>N</i>-phenylhydrazine-1-carbothioamide into 4-methyl-3-[2-(4-phenyl-5-sulfanylidene-4,5-dihydro-1<i>H</i>-1,2,4-triazol-3-yl)ethyl]quinolin-2(1<i>H</i>)-ones and 3-[2-(5-anilino-1,3,4-thiadiazol-2-yl)ethyl] 4-methylquino­lin-2(1<i>H</i>)-ones by heterocyclization in the presence of aqueous sodium hydroxide and concentrated sulfuric acid, respectively. The reactions are economically efficient, and the target products are formed in high yields (85–98%) under mild conditions without using expensive catalysts and column chromatography for their isolation.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1022 - 1027"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222311","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}
引用次数: 0
Hantzsch Synthesis of the Calcium Channel Blockers Nifedipine, Diludine, and Nitrendipine Using Methanesulfonic Acid as Catalyst 以甲磺酸为催化剂合成钙通道阻滞剂硝苯地平、地鲁定和尼群地平的汉兹合成法
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI: 10.1134/S1070428024060162
S. M. Potdar, S. S. Gurav, S. V. Raskar, K. T. Waghmode
{"title":"Hantzsch Synthesis of the Calcium Channel Blockers Nifedipine, Diludine, and Nitrendipine Using Methanesulfonic Acid as Catalyst","authors":"S. M. Potdar,&nbsp;S. S. Gurav,&nbsp;S. V. Raskar,&nbsp;K. T. Waghmode","doi":"10.1134/S1070428024060162","DOIUrl":"10.1134/S1070428024060162","url":null,"abstract":"<p>A simple and efficient one-pot three-component method has been developed and applied for the preparation of the calcium channel blockers nifedipine, diludine, and nitrendipine via Hantzsch dihydropyridine synthesis in good yields employing methanesulfonic acid as catalyst. The protocol stands out for mild reaction conditions, shorter reaction time, high yield, and easy workup and purification procedures, which enhance its practicality. Furthermore, the use of inexpensive and greener catalyst contributes to the efficacy and feasibility of the presented synthetic approach.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 6","pages":"1117 - 1122"},"PeriodicalIF":0.8,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142222338","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}
引用次数: 0
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