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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
Synthesis of Polysubstituted Furans from α-Substituted 2-Enals
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110095
V. G. Fedoseeva, E. A. Verochkina, L. I. Larina, N. V. Vchislo
{"title":"Synthesis of Polysubstituted Furans from α-Substituted 2-Enals","authors":"V. G. Fedoseeva,&nbsp;E. A. Verochkina,&nbsp;L. I. Larina,&nbsp;N. V. Vchislo","doi":"10.1134/S1070428024110095","DOIUrl":"10.1134/S1070428024110095","url":null,"abstract":"<p>The three-component reaction of cyclohexyl isocyanide, dimethyl acetylenedicarboxylate, and (<i>Z</i>)-3-phenyl-2-(alkylsulfanyl)- or (<i>Z</i>)-3-furyl-2-methoxyprop-2-enals gives polysubstituted furans in good yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2157 - 2161"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109295","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
Approaches to the Formation of the Key 2-Oxabicyclo[3.3.0]octan-3-one Precursor of Galiellalactone
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S107042802411006X
A. M. Gimazetdinov, V. V. Zagitov, Z. R. Makaev
{"title":"Approaches to the Formation of the Key 2-Oxabicyclo[3.3.0]octan-3-one Precursor of Galiellalactone","authors":"A. M. Gimazetdinov,&nbsp;V. V. Zagitov,&nbsp;Z. R. Makaev","doi":"10.1134/S107042802411006X","DOIUrl":"10.1134/S107042802411006X","url":null,"abstract":"<p>New vicinal all-<i>cis</i>-trisubstituted derivatives of cyclopentane- and cyclopentenetriols were synthesized.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2130 - 2139"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S107042802411006X.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143107899","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
Three-Component Synthesis of Novel 5H-[1,3]dioxolo[4,5-f]indole Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110174
Dan-Dan Wan, Ji Li, Jia-Yan Liu, Dong-Sheng Chen
{"title":"Three-Component Synthesis of Novel 5H-[1,3]dioxolo[4,5-f]indole Derivatives","authors":"Dan-Dan Wan,&nbsp;Ji Li,&nbsp;Jia-Yan Liu,&nbsp;Dong-Sheng Chen","doi":"10.1134/S1070428024110174","DOIUrl":"10.1134/S1070428024110174","url":null,"abstract":"<p>New 5<i>H</i>-[1,3]dioxolo[4,5-<i>f</i>]indole derivatives were synthesized in good yields were synthesized by a one-pot, three-component reaction of benzo[<i>d</i>][1,3]dioxol-5-amine, arylglyoxals, and 4-hydroxyquinolin-2(1<i>H</i>)-one in the presence of acetic acid as a catalyst in an ethanol medium under reflux.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2290 - 2297"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109680","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
Design, Synthesis, and Antibacterial Activity of Morpholine-4-sulfonamide Derivatives
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070428024110149
Huimin Zou, Yi Tan, Zhiyou Huang, Ping Yang, Wenxia Ou, Xiaohong Li
{"title":"Design, Synthesis, and Antibacterial Activity of Morpholine-4-sulfonamide Derivatives","authors":"Huimin Zou,&nbsp;Yi Tan,&nbsp;Zhiyou Huang,&nbsp;Ping Yang,&nbsp;Wenxia Ou,&nbsp;Xiaohong Li","doi":"10.1134/S1070428024110149","DOIUrl":"10.1134/S1070428024110149","url":null,"abstract":"<p>In the search for novel antibacterial agents, a series of <i>N</i>-(substituted nitrophenyl)morpholine-4-sulfonamides were prepared by the reactions of substituted nitrobenzenes with morpholine-4-sulfonamide under MW irradiation. The synthetic approach is characterized by a facile procedure and broad substrate scope. Preliminary biological assessment of the activity of compounds <b>1b–1h</b>, <b>1k–1n</b> against <i>Xanthomonas oryzae</i> pv. <i>oryzae</i> (<i>Xoo</i>) was higher than 80% at 800 μg/mL. Especially, the inhibition rate of compounds <b>1d</b>, <b>1k</b>, and <b>1n</b> were higher than 95%. Significantly, the EC<sub>50</sub> value of <b>1d</b> was close to the sanguinarine.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 11","pages":"2259 - 2265"},"PeriodicalIF":0.8,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109409","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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