Russian Journal of Organic Chemistry最新文献

{"title":"1,3,4-Thiadiazoles in Drug Discovery: Advances in Synthesis and Diverse Pharmacological Applications","authors":"P. Prajapati,&nbsp;S. Patel,&nbsp;P. Patel,&nbsp;H. Kardani,&nbsp;J. Thakkar,&nbsp;T. Barot,&nbsp;P. Vasava","doi":"10.1134/S1070428025604893","DOIUrl":"10.1134/S1070428025604893","url":null,"abstract":"<p>This review highlights recent advancements in the synthesis and pharmacological evaluation of 1,3,4-thiadiazole derivatives, with particular emphasis on green and efficient synthetic methodologies. The broad spectrum of biological activities exhibited by these compounds, including antimicrobial, anticancer, antioxidant, and anti-inflammatory properties, underlines the profound utility of the thiadiazole scaffold in medicinal chemistry and rational drug design. This comprehensive overview is intended to guide medicinal chemists in the rational development of novel, highly efficacious 1,3,4-thiadiazole-based lead compounds with optimized safety profiles. Furthermore, the clinical relevance of the 1,3,4-thiadiazole nucleus is discussed in the context of combating escalating multidrug resistance through the deployment of next-generation therapeutics.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 6","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927536","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":"Hydrostannation of Terminal Alkynes Catalyzed by Organozinc Compounds","authors":"Ziyuan Pang,&nbsp;Xin Wen,&nbsp;Yuhang Qiao,&nbsp;Xiaoli Ma,&nbsp;Zhi Yang","doi":"10.1134/S1070428025604972","DOIUrl":"10.1134/S1070428025604972","url":null,"abstract":"<p>The use of two economically viable and environmentally benign nonprecious-metal organozinc complexes as catalysts for the hydrostannation of terminal alkynes has been reported. Commercially available ZnEt₂ and a laboratory-prepared β-diketiminate ethylzinc complex LZnEt [L = HC(CMeNAr)₂, Ar = 2,6-(<i>i</i>-Pr)₂C₆H₃] exhibit excellent catalytic efficiency in the hydrostannation of terminal alkynes with Bu₃SnH, showing a broad substrate scope across aromatic, aliphatic, and alicyclic derivatives. Notably, ZnEt₂ demonstrates slightly higher catalytic activity than LZnEt, whereas the sterically demanding complex LZnEt provides enhanced stereoselectivity, which is attributed to its greater steric hindrance. A plausible mechanism for the ZnEt₂-catalyzed stannylation of terminal alkynes is proposed based on key reaction intermediates characterized by NMR spectroscopy.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 6","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927539","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":"Recent Advances in Chitosan-Based Organic Reactions","authors":"S. N. Mali,&nbsp;H. K. A. Yasin,&nbsp;R. Somani,&nbsp;B. Thorat","doi":"10.1134/S1070428025604121","DOIUrl":"10.1134/S1070428025604121","url":null,"abstract":"<p>Chitin and its partially deacetylated derivative, chitosan, are abundant natural biopolymers possessing unique structural and functional properties. Chitosan, characterized by its polycationic nature, biocompatibility, and pH-responsive solubility, offers distinct advantages over chitin regarding chemical reactivity and processability. These materials exhibit negligible toxicity and have been extensively utilized in biomedical, environmental, and catalytic applications. Their capacity to form coordination complexes, support catalytically active species, and interact with diverse biological and chemical systems highlights their versatility in modern materials science. This review provides a comprehensive overview of chitosan-based organic transformations documented in recent literature.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 6","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927540","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":"A New Synthetic Approach to Substituted Hydroquinoline-8-carboxylic Acids and 1,3-Oxazino[5,4,3-ij]quinolines","authors":"S. M. Medvedeva,&nbsp;A. V. Movchan,&nbsp;O. B. Rudakov,&nbsp;Kh. S. Shikhaliev","doi":"10.1134/S1070428026603213","DOIUrl":"10.1134/S1070428026603213","url":null,"abstract":"<p>Tricyclic systems derived from partially hydrogenated quinolines exhibit a broad spectrum of physiological activity. Biologically active compounds have also been identified among 1,3-oxazine derivatives. In particular, 1,3-oxazino[5,4,3-<i>ij</i>]quinolines exhibit antibacterial activity. This prompted us to construct novel tricyclic structures in which a 1,3-oxazine moiety is annulated to the hydroquinoline core at the <i>i</i>- and <i>j</i>-positions, expecting that such systems would exhibit broad-spectrum practical potential. To develop an efficient and a simple synthetic approach to 1,3-oxazino[5,4,3-<i>ij</i>]quinoline-1-ones, we performed an alternative synthesis of hydroquinoline-8-carboxylic acids and investigated their reaction with formaldehyde under various conditions. Substituted hydroquinoline-8-carboxylic acids, including previously undescribed ones, were prepared by alkaline hydrolysis of the corresponding 1,3-oxazino[5,4,3-<i>ij</i>]quinoline-1,3-diones. It was found that the reactions with formalin in boiling methanol in the when the quinolinecarboxylic acid contained a substituent on the aromatic ring. Under these conditions, substituted 1,3-oxazino[5,4,3-<i>ij</i>]quinolin-1-ones were obtained in yields of 60–76%. When paraformaldehyde was used as the cyclizing agent in the presence of zinc chloride, the reaction selectively proceeded selectively in methylene chloride at room temperature and was complete within 4 h. Neither presence nor the nature of substituents in the starting carboxylic acids significantly affected the reaction outcome; all target oxazinoquinolines were formed in high yields of 68–87%. These findings allowed us to develop a simple and an efficient two-stage protocol for the synthesis of substituted 1,3-oxazino[5,4,3-<i>ij</i>]quinoline-1-ones involving alkaline hydrolysis of 1,3-oxazino[5,4,3-<i>ij</i>]quinoline-1,3-diones to form hydroquinoline-8-carboxylic acids, followed by their acid-catalyzed cyclocondensation with formaldehyde or paraformaldehyde.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 8","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927381","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 and Antimicrobial Screening of 1-(Benzenesulfonyl)-3-chloro-4-haloaryl-4-methylazetidin-2-ones","authors":"M. Almehmdi,&nbsp;M. Asif","doi":"10.1134/S1070428025604212","DOIUrl":"10.1134/S1070428025604212","url":null,"abstract":"<p>A series of novel 1-(benzenesulfonyl)azetidin-2-one derivatives were synthesized and evaluated for their in vitro antimicrobial activity against a panel of bacterial and fungal strains. Halogen-substituted aceto­phenones were condensed with benzenesulfonamide to afford N-(1-haloarylethylidene)benzenesulfonamides <b>1a</b>–<b>1i</b>. Staudinger cycloaddition of these imine intermediates with chloroacetyl chloride yielded the target 1-(benzenesulfonyl)-3-chloro-4-(haloaryl)-4-methylazetidin-2-ones <b>2a</b>–<b>2i</b>. The structures of the synthesized compounds were fully elucidated using standard spectroscopic and analytical techniques. Antimicrobial screening via the agar disk diffusion method revealed that derivatives <b>2c</b>, <b>2d</b>, <b>2e</b>, <b>2g</b>, <b>2h</b>, and <b>2i</b> possess potent antibacterial activity, whereas compounds <b>2g</b>, <b>2h</b>, and <b>2i</b> exhibit pronounced antifungal efficacy. The enhanced antimicrobial profiles were attributed to the specific electronic and steric configurations of the haloaryl substituents on the azetidinone scaffold, which are likely to optimize binding interactions with microbial cellular targets. Compounds <b>2g</b>, <b>2h</b>, and <b>2i</b> represent promising lead candidates for the development of next-generation antibacterial and antifungal agents.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 6","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927579","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":"Conjugates of Sydnone Imines with Ligands of the Prostate-Specific Membrane Antigen","authors":"T. M. Voronov,&nbsp;A. S. Agafonov,&nbsp;N. V. Kalganova,&nbsp;I. A. Cherepanov,&nbsp;A. N. Vaneev,&nbsp;V. V. Mamed-Nabizade,&nbsp;Y. I. Guruleva,&nbsp;A. S. Erofeev,&nbsp;A. A. Uspenskaya,&nbsp;E. K. Beloglazkina,&nbsp;A. E. Machulkin","doi":"10.1134/S1070428026603456","DOIUrl":"10.1134/S1070428026603456","url":null,"abstract":"<p>In this study, a series of conjugates of the azide-containing PSMA ligand with substituted sydnone imines—NO donors that induce oxidative stress by increasing ROS (reactive oxygen species) levels—were synthesized. Conjugation was performed using CuAAC (copper-catalyzed azide-alkyne cycloaddition). The resulting conjugates were tested for cytotoxicity and ROS-generating capacity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 8","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927846","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":"N-Substituted Oxazolidines: Synthesis and Theoretical Evaluation of Anticorrosive Activity","authors":"E. S. Akimova,&nbsp;Yu. G. Borisova,&nbsp;S. S. Zlotskiy,&nbsp;J. Xing,&nbsp;J. Qian,&nbsp;R. M. Sultanova","doi":"10.1134/S1070428026602943","DOIUrl":"10.1134/S1070428026602943","url":null,"abstract":"<p>Corrosion of oil and gas field equipment caused by hydrogen sulfide and the metabolic activity of sulfate-reducing bacteria (SRP), in particular <i>Desulfovibrio desulfuricans</i>, remains one of the key problems of the industry. Existing corrosion inhibitors are often ineffective due to their toxicity and narrow spectrum of action. In this regard, the development of double-acting inhibitors based on heterocyclic structures is considered a promising approach. In this work, new derivatives of 1,3-oxazolidine have been synthesized. A theoretical assessment of their ability to simultaneously block corrosion processes on the metal surface and inhibit the vital activity of CRP has been performed using DFT, Fukui index calculation, and molecular docking. The obtained data suggest that the synthesized compounds can be regarded as promising candidates for developing environmentally safer and more effective corrosion inhibitors for hydrogen sulfide-containing media.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 8","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927384","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":"Reaction of 6,6-Dimethyl-5,6-dihydrobenzo[f]pyrrolo[2,1-a]isoquinoline-8,9-diones with Amino Alcohols and Aliphatic Diamines","authors":"N. N. Pershina,&nbsp;A. G. Мikhailovskii","doi":"10.1134/S1070428026603547","DOIUrl":"10.1134/S1070428026603547","url":null,"abstract":"<p>(<i>Z</i>)<i>-</i>3-(2,2-Dimethyl-2,3-dihydrobenzo[<i>f</i>]isoquinoline-4(1<i>H</i>)-ylidene)-<i>N</i>-(2-hydroxyethyl)-2-оxopropanamide was synthesized via the reaction of 10-R-6,6-dimethyl-5,6-dihydrobenzo[<i>f</i>]pyrrolo[2,1-<i>a</i>]isoquinoline-8,9-dione (R=H) with aminoethanol, and the same reaction with 3-aminopropanol afforded the corresponding <i>N</i>-(3-hydroxypropyl)amide. The starting dioxopyrroline with R = <i>N</i>-morpholinocarbonyl reacted under similar conditions: the reaction with ethylenediamine gave (3<i>Z</i>,3'<i>Z</i>)-<i>N</i>,<i>N'</i>-(ethane-1,2-diyl)bis(3-(2.2-dimethyl-2.3-dihydrobenzo[<i>f</i>]isoquinoline-4(1<i>H</i>)-ylidene)-2-oxopropanamide, and the reaction with hexamethylenediamine produced the corresponding hexane-1,6-diyl derivative. The reaction with 1,2-diaminocyclohexane involves pyrrole ring opening to form a hydrogenated benzimidazole derivative. The presence of an alcoholic hydroxyl in the amide moiety was confirmed by means of the benzoylation reaction.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 8","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927847","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, Characterization, Antimicrobial Activity, Cytotoxicity, and Molecular Docking Studies of 3-[(1-Phenyl-1H-1,2,3-triazol-4-yl)methoxy]adamantan-1-amine Derivatives","authors":"M. Nagu,&nbsp;B. Venkateswarlu","doi":"10.1134/S107042802560425X","DOIUrl":"10.1134/S107042802560425X","url":null,"abstract":"<p>A series of novel 1,2,3-triazole–adamantane hybrids were synthesized in 65–80% yields via cop­per(I)-catalyzed azide–alkyne cycloaddition (CuAAC). The structures of the target compounds were com­prehensively characterized using multinuclear NMR, IR, and mass spectrometry, alongside elemental analysis. Compounds <b>4e</b>, <b>4f</b>, and <b>4i</b> at a concentration of 100 μg/mL exhibited potent antibacterial activity against six distinct bacterial strains. Antifungal evaluation against four fungal strains revealed that compounds <b>4f</b> and <b>4i</b> possess robust broad-spectrum fungicidal efficacy, as evidenced by their high mean zone of inhibition values. Furthermore, in vitro cytotoxicity assays against MCF-7, PC-3, and HeLa human cancer cell lines demonstrated that derivatives <b>4b</b>, <b>4f</b>, <b>4i</b>, and <b>4k</b> markedly suppress cancer cell viability. In alignment with the experimental findings, molecular docking simulations indicated that compound <b>4f</b> consistently possesses the highest binding affinities against four key oncological protein targets: DHFR (–9.3 kcal/mol), enoyl reductase (–10.0 kcal/mol), Topo IIα (–9.2 kcal/mol), and ERα (–10.1 kcal/mol). Structural analysis of the docking poses revealed that <b>4f</b> establishes a network of critical hydrogen bonds and favorable nonpolar interactions within the binding pockets of all investigated proteins, highlighting its potential as a prominent multitarget anticancer lead.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 6","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927394","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 and Transformations of Oxazolidin-2-ones of the Adamantane Series","authors":"M. V. Leonova,&nbsp;Yu. N. Klimochkin","doi":"10.1134/S107042802660292X","DOIUrl":"10.1134/S107042802660292X","url":null,"abstract":"<p>An efficient one-step synthesis of previously unknown oxazolidin-2-one derivatives containing an adamantane moiety at the C-5 position of the heterocycle was achieved by reacting bromomethyloxiranes of the adamantane series with primary amines in the presence of potassium carbonate. The reaction proceeds through successive stages of nucleophilic substitution and intramolecular cyclization, providing the target products in yields of 40–80%. Several chemical transformations of the synthesized adamantyloxazolidin-2-ones were studied, including acidic hydrolysis accompanied by ring opening to form aminotriols, as well as the reactions of <i>N</i>-aminooxazolidinones with aromatic aldehydes and acid chlorides, leading to the corresponding hydrazones and acyl derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"62 8","pages":""},"PeriodicalIF":0.8,"publicationDate":"2026-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927484","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}