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Russian Journal of Organic Chemistry最新文献

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Synthesis and Analgesic Activity of 1-{(Z)-3-[(E)-3-Aryl-1-hydroxyallylidene]-2-oxochroman-4yl}cyclohexanecarboxylates 1-{(Z)-3-[(E)-3-芳基-1-羟基烯丙基]-2-氧铬-4基}环己anecarboxylates的合成及镇痛活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428026602293
E. A. Nikiforova, D. P. Zverev, M. V. Dmitriev, R. R. Makhmudov, N.F. Kirillov
{"title":"Synthesis and Analgesic Activity of 1-{(Z)-3-[(E)-3-Aryl-1-hydroxyallylidene]-2-oxochroman-4yl}cyclohexanecarboxylates","authors":"E. A. Nikiforova,&nbsp;D. P. Zverev,&nbsp;M. V. Dmitriev,&nbsp;R. R. Makhmudov,&nbsp;N.F. Kirillov","doi":"10.1134/S1070428026602293","DOIUrl":"10.1134/S1070428026602293","url":null,"abstract":"<p>The reaction of 3-(3-arylacryloyl)-2<i>H</i>-chromen-2-ones with a double excess of methyl 1-bromocyclohexanecarboxylate and zinc, followed by hydrolysis of the reaction mixture, yielded adducts across the double bond of the heterocyclic fragment, which exist in the enolic form. For more reliable signal assignment in the NMR spectra of the product, two-dimensional correlation spectroscopy (COSY, HSQC, and HMBC) was employed. The structures of the synthesized compounds were confirmed by X-ray crystallography data. The analgesic (antinociceptive) activity of the synthesized compounds was evaluated.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365893","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
Domino Transformation of Methyl 6-(6-Aryl-1,2,4-triazin-3-yl)picolinates upon Reaction with 2-Aminooxazoles 甲基6-（6-芳基-1,2,4-三嗪-3-基）吡啶甲酸酯与2-氨基唑反应的多米诺转化
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428025605692
E. D. Ladin, A. S. Alekseeva, A. S. Markina, A. V. Golovina, V. V. Chernyshov, P. A. Slepukhin, D. S. Kopchuk, G. V. Zyryanov
{"title":"Domino Transformation of Methyl 6-(6-Aryl-1,2,4-triazin-3-yl)picolinates upon Reaction with 2-Aminooxazoles","authors":"E. D. Ladin,&nbsp;A. S. Alekseeva,&nbsp;A. S. Markina,&nbsp;A. V. Golovina,&nbsp;V. V. Chernyshov,&nbsp;P. A. Slepukhin,&nbsp;D. S. Kopchuk,&nbsp;G. V. Zyryanov","doi":"10.1134/S1070428025605692","DOIUrl":"10.1134/S1070428025605692","url":null,"abstract":"<p>A new domino transformation during the high-temperature reaction of 2-amino-4-aryloxazoles with methyl 6-(1,2,4-triazin-3-yl)pyridine-2-carboxylates has been discovered. The transformation afforts methyl 3'-hydroxy-[2,4'-bipyridine]-6-carboxylates, which are scarcely accessible by other methods. A plausible mechanism of this process has been proposed. The structure of one of the products was confirmed by X-ray diffraction analysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365900","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, Characterization, and Biological Evaluation of Novel 2-{N-Phenyl-N-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]amino}benzenesulfonamide Derivatives 新型2-{n -苯基- n -[（1-苯基- 1h -1,2,3-三唑-4-基）甲基]氨基}苯磺酰胺衍生物的合成、表征和生物学评价
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428025604467
K. Tula, P. Kandukuri, R. Guguloth, S. P. Gadem, V. Namratha
{"title":"Synthesis, Characterization, and Biological Evaluation of Novel 2-{N-Phenyl-N-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]amino}benzenesulfonamide Derivatives","authors":"K. Tula,&nbsp;P. Kandukuri,&nbsp;R. Guguloth,&nbsp;S. P. Gadem,&nbsp;V. Namratha","doi":"10.1134/S1070428025604467","DOIUrl":"10.1134/S1070428025604467","url":null,"abstract":"<p>A novel series of 2-(<i>N-</i>phenyl-<i>N-</i>{[1-(R-phenyl)-1<i>H</i>-1,2,3-triazol-4-yl]methyl}amino)benzenesulfonamide derivatives was synthesized via the copper(I)-catalyzed azide–alkyne cycloaddition reaction of substituted alkynes with various aromatic azides. The structures of the synthesized compounds were confirmed by IR, <sup>1</sup>H NMR, and <sup>13</sup>C NMR spectroscopy and mass spectrometry. The antioxidant potential of the products was evaluated using DPPH and HRS assays. The highest activity in both antioxidant assays were demonstrated by the derivatives with R = 4-OH, 4-OMe, and 4-Me. These three compounds also exhibited impressive activities in the antimicrobial assay against Gram-positive (<i>B. subtilis</i> and <i>S. aureus</i>) and Gram-negative (<i>E. coli</i> and <i>S. typhi</i>) bacteria and <i>A. niger</i> and <i>C. albicans</i> fungi. The synthesized compounds were evaluated for their antiproliferative activity using the MTT assay against MCF-7 and PC-3 cell lines. In this assay, the strongest anticancer effect, comparable with that of the standard drug Doxorubicin, was demonstrated by the derivatives with R = 4-CN, 4-Me, and 4-CF<sub>3</sub>. The former two derivatives also showed the highest VEGFR2 binding affinities (–9.1 and –9.0 kcal/mol, respectively) in the molecular docking study, which provides a possible mechanistic rationale for their observed in vitro antiproliferative activity against MCF-7 and PC-3 cell lines.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365889","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
1,3,5-Trioxane and 1,3,5-Trithiane: Versatile Reagents for Heterocyclic Synthesis (A Review) 1,3,5-三氧环和1,3,5-三氧环：杂环合成的通用试剂（综述）
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428026600725
E. B. Rakhimova, V. Yu. Kirsanov
{"title":"1,3,5-Trioxane and 1,3,5-Trithiane: Versatile Reagents for Heterocyclic Synthesis (A Review)","authors":"E. B. Rakhimova,&nbsp;V. Yu. Kirsanov","doi":"10.1134/S1070428026600725","DOIUrl":"10.1134/S1070428026600725","url":null,"abstract":"<p>The review systematizes and summarizes recent advances in the synthesis of various classes of compounds using six-membered heterocycles―1,3,5-trioxane and 1,3,5-trithiane―as key reagents. The effect of reaction conditions on the formation of target compounds is considered, and some proposed reaction mechanisms are discussed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365897","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
Catalytic N-(Hetero)arylation of Camphan-2-amine and Fenchan-2-amine 樟脑-2胺和茴香-2胺的N-（杂）芳基化反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428026603729
V. I. Fomenko, D. S. Kuliukhina, D. A. Leksakov, A. D. Averin, A. A. Vernigora, I. A. Novakov, I. P. Beletskaya
{"title":"Catalytic N-(Hetero)arylation of Camphan-2-amine and Fenchan-2-amine","authors":"V. I. Fomenko,&nbsp;D. S. Kuliukhina,&nbsp;D. A. Leksakov,&nbsp;A. D. Averin,&nbsp;A. A. Vernigora,&nbsp;I. A. Novakov,&nbsp;I. P. Beletskaya","doi":"10.1134/S1070428026603729","DOIUrl":"10.1134/S1070428026603729","url":null,"abstract":"<p><i>N</i>-(Hetero)arylation of camphan-2-amine and fenchan-2-amine, which are characterized by a significant steric congestion of the amino group, was studied. It was shown that copper nanoparticles as a catalyst (10 mol %) in the presence of the <i>rac</i>-BINOL ligand provided 85–90% yields of the arylation products in the reaction with iodobenzene at 120°C, but were less effective in the reaction with bromobenzene. The reactions of camphan-2-amine with 2-halopyridines in the presence of the same catalytic system gave better results with 2-bromopyridine, yielding 74% of the target products, while the yields with fenchan-2-amine were lower. The efficiency of the copper-catalyzed amination was compared with reactions catalyzed by Pd(0). It was demonstrated that the Pd(dba)<sub>2</sub>/BINAP (4–8 mol %) catalytic system provided 78–94% yields of the <i>N</i>-phenyl- and <i>N</i>-pyridin-2-yl derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365894","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 and Pharmacological Evaluation of Novel Berberine Derivatives 新型小檗碱衍生物的合成及药理评价
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428025604194
S. Sangal, N. Dhama, A. Kumar, R. Pandey, N. Sharma
{"title":"Synthesis and Pharmacological Evaluation of Novel Berberine Derivatives","authors":"S. Sangal,&nbsp;N. Dhama,&nbsp;A. Kumar,&nbsp;R. Pandey,&nbsp;N. Sharma","doi":"10.1134/S1070428025604194","DOIUrl":"10.1134/S1070428025604194","url":null,"abstract":"<p>Berberine is an isoquinoline alkaloid with a broad spectrum of pharmacological activities, but it suffers from limited bioavailability and inferior physicochemical properties. In the current study, several novel berberine derivatives were rationally designed and synthesized by systematic structural modifications at the 8, 9, 12, and 13 positions of the berberine core. To impart enhanced lipophilicity and more favorable drug-like properties to the target novel berberine derivatives, we incorporated solubility-enhancing features via Grignard reactions, <i>O</i>-alkylation, Suzuki cross-coupling, and piperazine-based derivatization. All products were purified and structurally characterized by established methods. Antimicrobial screening against Gramnegative, Grampositive, and fungal strains showed that the substituent at C9 decisively modulates activity, and the synthetic approach reported here provides a practical route to diverse, more active berberine analogs, laying a foundation for future SAR studies and therapeutic development.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365895","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
Predicting Low-Hygroscopicity L-Carnitine Derivatives via Molecular Dynamics Simulations 通过分子动力学模拟预测低吸湿性左旋肉碱衍生物
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428025604583
Hyon-Tae Pak, Gyong-Hui Yun, Yun-Hui Ju, Yu-Chol Jong, Un-Ha Kim
{"title":"Predicting Low-Hygroscopicity L-Carnitine Derivatives via Molecular Dynamics Simulations","authors":"Hyon-Tae Pak,&nbsp;Gyong-Hui Yun,&nbsp;Yun-Hui Ju,&nbsp;Yu-Chol Jong,&nbsp;Un-Ha Kim","doi":"10.1134/S1070428025604583","DOIUrl":"10.1134/S1070428025604583","url":null,"abstract":"<p>L-Carnitine is a vital endogenous bioactive compound that facilitates mitochondrial fatty acid β-oxidation, rendering it essential for therapeutic and nutritional applications. However, its utilization is severely constrained by the highly hygroscopic nature of the L-carnitine zwitterion. While moisture-sorption behaviors of various environmental and pharmaceutical agents have been documented, a theoretical framework for mitigating L-carnitine hygroscopicity remains unexplored. Herein, we employ molecular dynamics simulations to establish a quantitative descriptor for evaluating the hygroscopicity of L-carnitine analogs and to predict moisture-stable derivative architectures. The intensity of the primary peak within 0.2 nm in the solute–water radial distribution function (RDF) was designated as the definitive hygroscopic index. Systematic structural screening based on this RDF descriptor identified calcium carnitine acetate and calcium carnitine fumarate as candidates with significantly suppressed hygroscopicity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365901","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
Sodium Bromate in Organic Synthesis: from Oxidation to Organic Transformations (A Review) 溴酸钠有机合成：从氧化到有机转化（综述）
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428025604996
Kiran Arora, Anshika Lumb, Reema Chhabra, Kalawati Meena, Deepti Rawat, Jitender M. Khurana
{"title":"Sodium Bromate in Organic Synthesis: from Oxidation to Organic Transformations (A Review)","authors":"Kiran Arora,&nbsp;Anshika Lumb,&nbsp;Reema Chhabra,&nbsp;Kalawati Meena,&nbsp;Deepti Rawat,&nbsp;Jitender M. Khurana","doi":"10.1134/S1070428025604996","DOIUrl":"10.1134/S1070428025604996","url":null,"abstract":"<p>Sodium bromate has emerged as a versatile reagent in recent decades. Beyond routine laboratory applications, it is utilized commercially in the dye industry, for sulfur oxidation, and in cosmetics. In combination with specific acids and salts, it serves as an efficient oxidant. Sodium bromate mediates the oxidation of benzylic positions to alcohols, as well as primary and secondary alcohols to their corresponding aldehydes and ketones. Furthermore, sulfides, tellurides, and phosphines are efficiently converted to sulfoxides, sulfones, telluroxides, and phosphine oxides, respectively. Sodium bromate has also demonstrated high efficacy in various transformations facilitated by ionic liquids. Its high stability, low cost, and ready availability make it an attractive oxidant and brominating agent. These reactions are typically performed at room temperature across various media, with optimal results generally achieved in acetonitrile, aqueous acetonitrile, or water alone. In addition to its industrial utility in cosmetics, dyeing, and gold ore processing, the use of sodium bromate in organic synthesis warrants further exploration as a cost-effective, easily handled alternative to elemental bromine.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148380168","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
Optimized Synthesis of (1Z)-1-Bromo-3,3,3-trichloro-1-nitropropene and Its Reaction with Indoles （1Z）-1-溴-3,3,3-三氯-1-硝基丙烯的优化合成及其与吲哚的反应
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428025605801
I. A. Pilipenko, A. S. Smirnov, O. Yu. Ozerova, R. I. Baichurin, S. V. Makarenko
{"title":"Optimized Synthesis of (1Z)-1-Bromo-3,3,3-trichloro-1-nitropropene and Its Reaction with Indoles","authors":"I. A. Pilipenko,&nbsp;A. S. Smirnov,&nbsp;O. Yu. Ozerova,&nbsp;R. I. Baichurin,&nbsp;S. V. Makarenko","doi":"10.1134/S1070428025605801","DOIUrl":"10.1134/S1070428025605801","url":null,"abstract":"<p>A modified method for the synthesis of (1<i>Z</i>)-1-bromo-3,3,3-trichloro-1-nitropropene has been proposed. The reactions of this compound with indole and <i>N</i>-methylindole lead to the formation of substitution–addition products. The structures of all products were confirmed by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, and the structures of (1<i>E</i>)-3,3,3-trichloro-1-nitropropene and (1<i>Z</i>)-1-bromo-3,3,3-trichloro-1-nitropropene were additionally verified by <sup>1</sup>H–<sup>15</sup>N HMBC NMR spectroscopy.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365890","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
New Enamines Derived from Methyl 2,4-Dioxo-4-arylbutanoates and 4-Aminoazobenzene: Synthesis and Study of Their Cyclization under the Action of Oxalyl Chloride 由2,4-二氧基-4-芳基丁酸甲酯和4-氨基偶氮苯衍生的新胺：草酰氯作用下的合成及其环化研究
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2026-07-03 DOI: 10.1134/S1070428026602451
D. V. Dzheparov, E. S. Denislamova, M. V. Dmitriev, A. N. Maslivets
{"title":"New Enamines Derived from Methyl 2,4-Dioxo-4-arylbutanoates and 4-Aminoazobenzene: Synthesis and Study of Their Cyclization under the Action of Oxalyl Chloride","authors":"D. V. Dzheparov,&nbsp;E. S. Denislamova,&nbsp;M. V. Dmitriev,&nbsp;A. N. Maslivets","doi":"10.1134/S1070428026602451","DOIUrl":"10.1134/S1070428026602451","url":null,"abstract":"<p>New acyclic enamines—methyl (<i>Z</i>)-4-oxo-4-phenyl-2-{[4-((<i>E</i>)-phenyldiazenyl)phenyl]amino}but-2-enoates—were synthesized by reacting equimolar amount of methyl 2,4-dioxo-4-arylbutanoates with 4-aminoazobenzene in methanol.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 5","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148365892","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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