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Synthesis of (Carboxymethylidene)cyclopentenedione Derivatives via the Oxidative Cleavage of the Allylic Double Bond in 2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110186
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov
{"title":"Synthesis of (Carboxymethylidene)cyclopentenedione Derivatives via the Oxidative Cleavage of the Allylic Double Bond in 2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione","authors":"V. A. Egorov,&nbsp;L. S. Khasanova,&nbsp;F. A. Gimalova,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428024110186","DOIUrl":"10.1134/S1070428024110186","url":null,"abstract":"<p>The oxidative cleavage reactions of the allylic double bond in 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione in the OsO<sub>4</sub>–NaIO<sub>4</sub> and KMnO<sub>4</sub>–Et<sub>3</sub>BnN<sup>+</sup>Cl<sup>–</sup> systems were studied. The periodate cleavage of the starting 2-allylcyclopentene-1,3-dione gave an aldehyde, whose oxidation with the Jones reagent followed by HCl elimination resulted in the formation of the target 2-(carboxymethylidene)cyclopent-4-ene-1,3-dione. In the alternative approach, the permanganate oxidation of the starting 2-allylcyclopentene-1,3-dione led to the corresponding diol in a moderate yield.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2298 - 2301"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109679","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 Analgesic Activity of Substituted N-Alkyl-4-aryl-2-aroylhydrazylidene-4-oxobutanamides
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110101
E. I. Denisova, O. V. Zvereva, D. V. Lipin, R. R. Makhmudov, I. N. Chernov, E. S. Denislamova, D. A. Shipilovskikh, N. M. Igidov
{"title":"Synthesis and Analgesic Activity of Substituted N-Alkyl-4-aryl-2-aroylhydrazylidene-4-oxobutanamides","authors":"E. I. Denisova,&nbsp;O. V. Zvereva,&nbsp;D. V. Lipin,&nbsp;R. R. Makhmudov,&nbsp;I. N. Chernov,&nbsp;E. S. Denislamova,&nbsp;D. A. Shipilovskikh,&nbsp;N. M. Igidov","doi":"10.1134/S1070428024110101","DOIUrl":"10.1134/S1070428024110101","url":null,"abstract":"<p>A series of new substituted derivatives of <i>N</i>-alkyl-4-aryl-2-aroylhydrazylidene-4-oxobutanamides were synthesized via the opening of the furan ring in substituted 3-<i>N</i>-5-aryl-2-oxofuran-3(2<i>H</i>)-ylidene-4-R<sup>1</sup>-benzohydrazides under the action of various alkylamines. The in vivo analgesic activity and acute toxicity of the synthesized compounds were assessed to show that they have a pronounced analgesic activity and are almost nontoxic.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2162 - 2169"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109288","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 C3 Alkylation of the Furan/Thiophene Ring in 2-(Furan-2-carbonyl)/(Thiophene-2-carbonyl)-1-methylimidazoles with Acrylic Acid Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110071
K. E. Shepelenko, I. G. Gnatiuk, V. M. Chernyshev
{"title":"Ruthenium-catalyzed C3 Alkylation of the Furan/Thiophene Ring in 2-(Furan-2-carbonyl)/(Thiophene-2-carbonyl)-1-methylimidazoles with Acrylic Acid Derivatives","authors":"K. E. Shepelenko,&nbsp;I. G. Gnatiuk,&nbsp;V. M. Chernyshev","doi":"10.1134/S1070428024110071","DOIUrl":"10.1134/S1070428024110071","url":null,"abstract":"<p>A method for the synthesis of 3-alkyl-2-(furan-2-carbonyl)/(thiophene-2-carbonyl)-1-methylimidazoles by the ruthenium-catalyzed selective C<sup>3</sup> alkylation of the furan or thiophene ring in 2-(furan-2-carbonyl)/(thiophene-2-carbonyl)-1-methylimidazoles with acrylic acid esters, amides, or nitrile has been developed. The resulting compounds may be of interest as polyfunctional reagents for preparing 3-(2-carboxyethyl)furan/thiophene-2-carboxylic acid derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2140 - 2146"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109294","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
Substituted-1,3,4-oxadiazole Indole Derivatives: Design, Synthesis, Characterization, and Evaluation of the Antimicrobial and Anti-Inflammatory Activities
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110162
Medarametla Venkatesh, Chappidi Hazarathaiah Yadav, Mavallur Varalakshmi
{"title":"Substituted-1,3,4-oxadiazole Indole Derivatives: Design, Synthesis, Characterization, and Evaluation of the Antimicrobial and Anti-Inflammatory Activities","authors":"Medarametla Venkatesh,&nbsp;Chappidi Hazarathaiah Yadav,&nbsp;Mavallur Varalakshmi","doi":"10.1134/S1070428024110162","DOIUrl":"10.1134/S1070428024110162","url":null,"abstract":"<p>In view of the significant biological potency of indole derivatives and 1,3,4-oxadiazoles, in the present work we synthesized a new series of indole-based substituted 1,3,4-oxadiazole derivatives, specifically 1-[5-(1<i>H</i>-indol-5-yl)-2-substituted-1,3,4-oxadiazol-3(2<i>H</i>)-yl]ethenones from 1<i>H</i>-indole-5-carboxylic acid through a sequence of reactions. All the synthesized compounds were evaluated for their antimicrobial and ant-inflammatory activities. The results of the antimicrobial assay showed that most of the products exhibited promising activity against the tested bacterial strains, especially <i>P. aeruginosa</i> (ATCC27853) with MIC 6.25 μg/mL, whereas very few compounds showed a high antifungal activity with MICs ranging from 6.25 to 50.0 μg/mL. All the synthesized compounds showed a low to moderate antiinflammatory activity with the albumin denaturation inhibition activity of &lt; 66%, which is lower than that of the standard drug diclofenac (85.5%). Overall, the biological testing showed that the indole-based substituted 1,3,4-oxadiazole derivatives act as potent antibacterial rather than anti-inflammatory agents, and their activity can be enhanced by the introduction of an appropriate pharmacophoric substituent in the 1,3,4-oxadiazole motif.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2276 - 2289"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109414","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
Development of 2-(Trifluoromethyl)pyridine Peptide Derivatives: Synthesis and Computational Studies
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110150
N. Sagar, R. Hadavani, S. Bijani, P. Vadodariya, V. Narula, Y. Jadeja, V. Jain
{"title":"Development of 2-(Trifluoromethyl)pyridine Peptide Derivatives: Synthesis and Computational Studies","authors":"N. Sagar,&nbsp;R. Hadavani,&nbsp;S. Bijani,&nbsp;P. Vadodariya,&nbsp;V. Narula,&nbsp;Y. Jadeja,&nbsp;V. Jain","doi":"10.1134/S1070428024110150","DOIUrl":"10.1134/S1070428024110150","url":null,"abstract":"<p>Herein we report the synthesis and characterization of pyridine–peptide conjugates containing a trifluoromethyl group by a the acid–amine coupling reaction between (<i>E</i>)-3-[6-(trifluoromethyl)pyridin-3-yl]acrylic acid and various amino acids. The synthetic route involves a straightforward acid–amine coupling reaction. The resulting conjugates were characterized by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry. To evaluate the antibacterial and antimalarial potentials of the synthesized conjugates, we performed their molecular docking to <i>Mycobacterium tuberculosis</i> enoyl-ACP reductase (PDB ID: 4TZK), <i>Pseudomonas aeruginosa</i> LysR-type transcriptional regulator (PDB ID: 7NBW), and <i>Plasmodium falciparum</i> dihydrofolate reductase-thymidylate synthase (PDB ID: 3QG2) was used to elucidate the ligand–protein binding modes, intermolecular interactions, and affinities, which was also used to assess and justify the stability of the ligands in the receptor site. The computational study allowed us to identify the products with potential antimalarial and anti-tubercular properties and favourable ADMET profiles, among which (<i>E</i>)-(<i>N</i>-{3-[6-(Trifluoromethyl)pyridin-3-yl]acryloyl}prolyl)phenylalanine showed strong binding affinities to multiple targets).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2266 - 2275"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109417","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
Substituted Ureas and Their Analogs Containing Framework Fragments: I. 1-(4-Hydroxyadamantan-1-yl)-3-(fluoro/chlorophenyl)ureas
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110034
D. V. Danilov, V. S. D’yachenko, D. M. Zapravdina, E. S. Ilyina, E. K. Degtyarenko, V. V. Burmistrov
{"title":"Substituted Ureas and Their Analogs Containing Framework Fragments: I. 1-(4-Hydroxyadamantan-1-yl)-3-(fluoro/chlorophenyl)ureas","authors":"D. V. Danilov,&nbsp;V. S. D’yachenko,&nbsp;D. M. Zapravdina,&nbsp;E. S. Ilyina,&nbsp;E. K. Degtyarenko,&nbsp;V. V. Burmistrov","doi":"10.1134/S1070428024110034","DOIUrl":"10.1134/S1070428024110034","url":null,"abstract":"<p>A series of 1,3-disubstituted ureas containing a 4-(hydroxyadamantan-1-yl)-fragment were synthesized in yields of 55–87% by the reaction of 1-(4-oxoadamantan-1-yl)-3-(halophenyl)ureas with sodium borohydride . The synthesized ureas are potential metabolites and promising soluble human epoxide hydrolase inhibitors.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2108 - 2116"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024110034.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143107898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Reactions of 2-Amino-3-Cyanopyridine Derivatives (A Review)
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110113
K. E. Anwer, G. H. Sayed
{"title":"Synthesis and Reactions of 2-Amino-3-Cyanopyridine Derivatives (A Review)","authors":"K. E. Anwer,&nbsp;G. H. Sayed","doi":"10.1134/S1070428024110113","DOIUrl":"10.1134/S1070428024110113","url":null,"abstract":"<p>Pyridine is a versatile lead compound for designing potent bioactive agents. This review is devoted to the synthesis of enaminonitrile pyridines by different methods, including one-pot multicomponent and ultrasound- and microwave-assisted reactions, from primary amines, enaminonitrile pyrazole, arylidene nitriles, and chalcones. The review also considers the chemical reactivity of enaminonitrile pyridines toward organic compounds of different classes, as well as their diverse biological activities.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2170 - 2227"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109287","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 Functionalized Spiro[1-benzofuran-2,5'-pyrimidine] Derivatives of 5-Arylidenebarbituric Acids
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110058
A. N. Andin, M. A. Engelgardt
{"title":"Synthesis of Functionalized Spiro[1-benzofuran-2,5'-pyrimidine] Derivatives of 5-Arylidenebarbituric Acids","authors":"A. N. Andin,&nbsp;M. A. Engelgardt","doi":"10.1134/S1070428024110058","DOIUrl":"10.1134/S1070428024110058","url":null,"abstract":"<p>Adducts of dimedone and 5-arylidenebarbituric acids react with <i>N</i>-bromosuccinimide in aqueous ethanol to give functionalized spiro[1-benzofuran-2,5'-pyrimidine] derivatives with moderate yields. The reaction of 5-benzylidenebarbituric acid with ethyl acetoacetate in the presence of <i>N</i>-bromosuccinimide provides spiro[pyrimidine-5,6'-furo[2,3-<i>d</i>]pyrimidine].</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2125 - 2129"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024110058.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Antioxidant Activity of N-Substituted Diamides Based on Ethyl N-(2-Allyl-2-arylpent-4-en-1-yl)oxamate
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110046
A. A. Aghekyan, G. G. Mkryan, G. V. Stepanyan, H. A. Panosyan, H. A. Pahutyan, H. V. Gasparyan, A. B. Sargsyan
{"title":"Synthesis and Antioxidant Activity of N-Substituted Diamides Based on Ethyl N-(2-Allyl-2-arylpent-4-en-1-yl)oxamate","authors":"A. A. Aghekyan,&nbsp;G. G. Mkryan,&nbsp;G. V. Stepanyan,&nbsp;H. A. Panosyan,&nbsp;H. A. Pahutyan,&nbsp;H. V. Gasparyan,&nbsp;A. B. Sargsyan","doi":"10.1134/S1070428024110046","DOIUrl":"10.1134/S1070428024110046","url":null,"abstract":"<p>The reactions of 2-allyl-2-arylpent-4-en-1-amines with diethyl oxalate were used to synthesize ethyl oxamates, which were further reacted with nonaromatic amines to obtain the corresponding diamides. To synthesize aryl-substituted oxamides, the same amines are reacted with ethyl N-aryloxamates. The antioxidant activity of the synthesized diamides was studied.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2117 - 2124"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109416","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
Fly Ash:Sulfated Bi2O3-catalyzed Synthesis of Bioactive Arylimines and Arylamines
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110137
S. Nalini, P. Gayathri, J. Divya, I. Muthuvel, K. Thirumurthy, P. Mayavel, N. Dinesh Kumar, G. Thirunarayanan
{"title":"Fly Ash:Sulfated Bi2O3-catalyzed Synthesis of Bioactive Arylimines and Arylamines","authors":"S. Nalini,&nbsp;P. Gayathri,&nbsp;J. Divya,&nbsp;I. Muthuvel,&nbsp;K. Thirumurthy,&nbsp;P. Mayavel,&nbsp;N. Dinesh Kumar,&nbsp;G. Thirunarayanan","doi":"10.1134/S1070428024110137","DOIUrl":"10.1134/S1070428024110137","url":null,"abstract":"<p>Series of arylimines and arylamines were synthesized by the fly ash:sulfated Bi<sub>2</sub>O<sub>3</sub><b>-</b>catalyzed condensations of amines and aldehydes or 3-aminocarbazole and aryl enones under MW irradiation in solvent-free conditions in yields of higher than 60%. The synthesized compounds were characterized by their physical constants and spectroscopic data. The XRD structure of one of the synthesized imines, specifically (<i>E</i>)-<i>N</i>-(2,5-dimethoxybenzylidene)-2-phenoxyaniline imine was obtained. A molecular docking study of the synthesized arylimines and arylamines was performed, and their antimicrobial and antimalarial activities were assessed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2242 - 2258"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109285","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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