{"title":"Base-Catalyzed One-Pot Synthesis of Tetrahydrofuropyridinone Derivatives. Antioxidant and Molecular Docking Studies","authors":"N. Sadaria, V. Jain, V. M. Khedkar, J. Makasana","doi":"10.1134/S1070428024604503","DOIUrl":"10.1134/S1070428024604503","url":null,"abstract":"<p>A convenient one-pot synthesis of a novel series of 3-aryl-2-[4-(methylsulfanyl)benzoyl]-2,3,6,7-tetrahydrofuro[3,2-<i>c</i>]pyridin-4(5<i>H</i>)-ones <b>4a</b>–<b>4j</b> by reacting piperidine-2,4-dione, 4-(methylsulfanyl)phenacyl bromide, and various aromatic aldehydes in the presence of a dual catalyst (triethylamine/pyridine) has been developed. The compounds were well characterized by spectroscopic techniques and evaluated for their antioxidant activity. Compounds <b>4a</b>, <b>4c</b>, and <b>4d</b> exhibited excellent radical scavenging activity (IC<sub>50</sub> = 656.2, 648.2, and 660.8 µM, respectively) compared to ascorbic acid (IC<sub>50</sub> = 703.2 µM). Molecular docking studies were also performed against the enzyme myeloperoxidase to gain insights into the mechanistic basis for the antioxidant activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"721 - 730"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143551","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}
D. M. Zapravdina, E. A. Eshtukova-Shcheglova, E. V. Yakovleva, I. E. Nazarov, E. S. Ilyina, E. N. Savelyev, V. V. Burmistrov
{"title":"Substituted Ureas and Their Analogs Containing Cage Fragments: II. N,N′-(4-(Adamantan-1-yl)-1,2-phenylene)bis[N′-(R-phenyl)ureas and -thioureas]","authors":"D. M. Zapravdina, E. A. Eshtukova-Shcheglova, E. V. Yakovleva, I. E. Nazarov, E. S. Ilyina, E. N. Savelyev, V. V. Burmistrov","doi":"10.1134/S1070428024604904","DOIUrl":"10.1134/S1070428024604904","url":null,"abstract":"<p><i>N</i>,<i>N</i>′-Disubstituted bis-ureas and bis-thioureas containing a 4-(adamantan-1-yl)-1,2-phenylene spacer have been synthesized in 66–93% yields by the reaction of 4-(adamantan-1-yl)benzene-1,2-diamine with aromatic isocyanates and isothiocyanates. It has been found that no addition of a base (triethylamine) is required to achieve a high conversion within 12 h. The proposed method makes it possible to simplify the synthesis, isolation, and purification of the target compounds.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"580 - 586"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143570","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}
{"title":"Design, Synthesis, and Antitumor Activity of Erianin Derivatives","authors":"Bailing Jiang, Siqi Wang, Caiju Wu, Yifei Gu","doi":"10.1134/S1070428024600196","DOIUrl":"10.1134/S1070428024600196","url":null,"abstract":"<p>Erianin, despite its potent anticancer effects against various cancer cell lines, suffers from poor bioavailability due to limited solubility and rapid metabolism. To overcome these limitations, a series of novel erianin derivatives were designed, synthesized, and evaluated for their biological activities against HeLa, MDA-MB-231, and A498 cancer cell lines. Among these derivatives, compound <b>8j</b>, 4-[6,7-dimethoxy-3,4-dihydroisoquinolin-2(1<i>H</i>)-yl]-<i>N</i>-(4-methoxybenzyl)-4-oxo-<i>N</i>-(3,4,5-trimethoxyphenyl)butanamide, demonstrated the highest selectivity and most potent activity against HeLa cells with an IC<sub>50</sub> value of 7.53±3.57 μM. Compound <b>8j</b> significantly inhibited the adhesion, proliferation, migration, and invasion of HeLa cells in a dose-dependent manner. Preliminary pharmacokinetic evaluations suggest favorable absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties consistent with drug-like behavior. Molecular docking studies further revealed that <b>8j</b> binds to the colchicine-binding site of tubulin, indicating its potential mechanism of action. These findings suggest that compound <b>8j</b> is a promising lead candidate for the development of novel anticancer agents targeting the colchicine-binding site on tubulin.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"731 - 742"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143572","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}
{"title":"Unexpected Formation of Allylic Hydroxylation Product in the Ozonolysis of N-[2-(Cyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide","authors":"R. R. Safargalin, R. R. Gataullin","doi":"10.1134/S1070428025600299","DOIUrl":"10.1134/S1070428025600299","url":null,"abstract":"<p>The ozonolysis of <i>N</i>-[(2-cyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide, followed by treatment with dimethyl sulfide gave a mixture of the expected keto aldehyde, 4-methyl-<i>N</i>-[2-methyl-6-(6-oxohexanoyl)phenyl]benzenesulfonamide and unexpected allylic hydroxylation product, <i>N</i>-[2-(6-hydroxycyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"635 - 639"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143577","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}
{"title":"Synthesis of Substituted 2-Arylimino-3-oxopropanenitriles and 2-(Arylimino)propanedinitriles by Oxidative Coupling of Primary Aromatic Amines with Aroylacetonitriles and Malononitrile","authors":"A. V. Kachanov, M. A. Kucheshov, O. Yu. Slabko","doi":"10.1134/S1070428025601074","DOIUrl":"10.1134/S1070428025601074","url":null,"abstract":"<p>Oxidative coupling of aromatic amines with 3-aryl-3-oxopropanenitriles in the presence of selenium(IV) oxide gave the corresponding 2-arylimino-3-oxopropanenitriles. Similar reactions of arylamines with propanedinitrile afforded 2-(arylimino)propanedinitriles.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"669 - 674"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143578","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}
E. N. Ramskaya, A. Yu. Alekseeva, S. V. Zhitar, N. N. Yashchenko, E. G. Zinovieva, I. N. Bardasov
{"title":"Synthesis and Optical Properties of 6-Alkylamino-2-amino-4-[(4-(dimethylamino)phenyl]pyridine-3,5-dicarbonitriles","authors":"E. N. Ramskaya, A. Yu. Alekseeva, S. V. Zhitar, N. N. Yashchenko, E. G. Zinovieva, I. N. Bardasov","doi":"10.1134/S1070428025600743","DOIUrl":"10.1134/S1070428025600743","url":null,"abstract":"<p>2-Amino-6-chloro-4-[4-(dimethylamino)phenyl]pyridine-3,5-dicarbonitrile was synthesized in three steps starting from <i>N</i>,<i>N</i>-dimethylaniline, and its reactions with primary and secondary amines afforded 6-alkylamino-2-amino-4-[4-(dimethylamino)phenyl]pyridine-3,5-dicarbonitriles. The latter showed fluorescence in solution with an emission maximum in the range of λ 432–473 nm and a quantum yield of up to 29.5%, as well as solid-state fluorescence with a maximum in the range of λ 446–472 nm.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"640 - 646"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145144036","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}
K. A. Frolov, B. S. Krivokolysko, N. A. Aksenov, S. G. Krivokolysko
{"title":"Synthesis of (2E,4E)-2-(4-Aryl-1,3-selenazol-2-yl)-5-phenylpenta-2,4-dienenitriles","authors":"K. A. Frolov, B. S. Krivokolysko, N. A. Aksenov, S. G. Krivokolysko","doi":"10.1134/S1070428025600366","DOIUrl":"10.1134/S1070428025600366","url":null,"abstract":"<p>(2<i>E</i>,4<i>E</i>)-2-Cyano-5-phenylpenta-2,4-dieneselenoamide reacted with α-bromo ketones in DMF under argon to give (2<i>E</i>,4<i>E</i>)-2-(4-aryl-1,3-selenazol-2-yl)-5-phenylpenta-2,4-dienenitriles in 42–71% yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"621 - 624"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145144037","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}
{"title":"Fe3O4@Sal@Cu as a Novel Multifunctional Magnetic Nanocatalyst for Clean and Mild Synthesis of 2,3-Dihydro-1H-perimidines","authors":"R. Ferdosian, F. K. Behbahani, B. Mohtat","doi":"10.1134/S1070428024603315","DOIUrl":"10.1134/S1070428024603315","url":null,"abstract":"<p>Fe<sub>3</sub>O<sub>4</sub>@Sal@Cu magnetic nanoparticles were synthesized and used as a novel multifunctional nanocatalyst for the synthesis of 2,3-dihydro-1<i>H</i>-perimidines by the condensation of naphthalene-1,8-diamine with various aromatic aldehydes under ultrasonication. This efficient methodology has advantages such as good to excellent yields, high purity of the products, reusability of the nanocatalyst, simple reaction conditions, environmental friendliness, and economical chemical procedure.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"689 - 695"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143579","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}
{"title":"Green Solvent-Free Synthesis of Biologically Relevant Heterocycles—A Mini Review","authors":"M. Dinodia","doi":"10.1134/S1070428024604163","DOIUrl":"10.1134/S1070428024604163","url":null,"abstract":"<p>There has been a significant increase in the development of synthetic strategies to obtain various heterocyclic moieties. This area of research is particularly attractive because many heterocycles exhibit biological activity. Conventional techniques often involve the use of volatile organic solvents, which are typically flammable, toxic, and environmentally hazardous. These solvents are now being replaced either with greener alternatives or by completely eliminating their use. Numerous solvent-free methods for the synthesis of bioactive heterocyclic compounds have already been reported in the literature. This mini-review highlights recent advances in solvent-free synthetic methods for the preparation of diverse heterocycles with various biological activities.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 4","pages":"675 - 688"},"PeriodicalIF":0.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143851","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}