Russian Journal of Organic Chemistry最新文献

{"title":"Mass Spectra of New Heterocycles: XXVII. Electron Ionization Study of Polysubstituted 4,4′-Dipyrromethanes","authors":"L. V. Klyba,&nbsp;E. R. Sanzheeva,&nbsp;N. A. Nedolya,&nbsp;O. A. Tarasova","doi":"10.1134/S1070428024120042","DOIUrl":"10.1134/S1070428024120042","url":null,"abstract":"<p>The behavior of a series of polysubstituted 4,4′-dipyrromethanes, namely 1,1′-bis{2-amino-1-[2-(vinyloxy)ethyl]-5-sulfanyl-1<i>H</i>-pyrrol-4-yl}ethanes, under electron impact (70 eV) has been studied for the first time. The title compounds were synthesized in one preparative step from propargylamines, 2-(vinyloxy)ethyl isothiocyanate, and alkylating agents. Except for 5,5′-bis[(allyl-, propargyl-, and cyanomethyl)sulfanyl]­dipyrromethanes, the examined compounds give rise to stable molecular ions which decompose along three main pathways with the formation of four key cations. Two fragmentation pathways involve cleavage of the C–S bonds in the sulfanyl substituent and with the pyrrole ring to produce [<i>M</i> – R²]⁺ and [<i>M</i> – SR²]⁺ ions, respectively. The third pathway is associated with cleavage of the C–C bond between the pyrrole ring and methylene bridge connecting the pyrrole ring. In this case, two ions can be formed with the abundance ranging from 3 to 100%, depending on the substituent structure. The most abundant (up to 100% relative intensity) are radical cations [<i>M</i> – R² – SR²]^+<b>·</b>. The resulting fragment ions are stabilized via cyclization involving the vinyloxyethyl group.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2336 - 2344"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361953","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 Detecting Properties of New Linear and Macrocyclic O,O′-Aminobenzyl BINOL Derivatives","authors":"A. D. Sergeev,&nbsp;A. A. Yakushev,&nbsp;A. S. Malysheva,&nbsp;A. D. Averin,&nbsp;I. P. Beletskaya","doi":"10.1134/S1070428024120017","DOIUrl":"10.1134/S1070428024120017","url":null,"abstract":"<p>A series of <i>O</i>-halobenzyl and <i>O</i>,<i>O</i>′-bis(halobenzyl) derivatives of (<i>S</i>)-1,1′-bi(2-naphthol) (BINOL) have been synthesized, and their amination in the presence of palladium and copper catalysts has been studied. As a result, a new family of macrocyclic and linear BINOL derivatives with various substituents at the oxygen atoms, including those possessing additional chiral centers, has been obtained. The synthesized compounds have been evaluated for their detecting properties toward metal cations by UV and fluorescence titration. Among the obtained open-chain derivatives, a potential fluorescent sensor for Al³⁺ cations has been found due to multiple emission enhancement. In addition, a fluorescent molecular probe for Hg²⁺ and Al³⁺ has been identified. Among the macrocyclic derivatives, the compound with the longest trioxadiamine linker can be used as a molecular probe for Mg²⁺ and Ca²⁺ ions due to fluorescence enhancement with a red shift, as well as for Al³⁺ and Hg²⁺ ions due to strong fluorescence enhancement without change of the position of the emission maximum.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2305 - 2320"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024120017.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362010","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}

{"title":"Synthesis of Novel Triazolethione-, Thiadiazole-, and Triazole-Functionalized Quinazolin-4(3H)-one Derivatives and Their Antimicrobial Activity and Docking Studies","authors":"R. Dasari,&nbsp;S. Gali,&nbsp;R. Korra,&nbsp;N. Vaddiraju","doi":"10.1134/S1070428024120200","DOIUrl":"10.1134/S1070428024120200","url":null,"abstract":"<p>A series of novel triazolethione-, thiadiazole-, and triazole-functionalized quinazolin-4(3<i>H</i>)-one derivatives have been synthesized from 2-amino-6-(trifluoromethyl)benzonitrile (<b>1</b>). The acid hydrolysis of <b>1</b> gave 2-amino-6-(trifluoromethyl)benzoic acid (<b>2</b>) which was cyclized with trifluoroacetamide to obtain 2,5-bis(trifluoromethyl)quinazolin-4(3<i>H</i>)-one (<b>3</b>). Compound <b>3</b> was alkylated with ethyl 2-bromoacetate, and treatment of the resulting ethyl 2-[4-oxo-2,5-bis(trifluoromethyl)-3,4-dihydroquinazolin-3-yl]acetate (<b>4</b>) with hydrazine hydrate produced the corresponding acetohydrazide <b>5</b>. The latter reacted with substituted phenyl isothiocyanates to afford thiourea derivatives <b>6</b> which were converted to triazolethione-, thiadiazole-, and triazole-functionalized quinazolin-4(3<i>H</i>)-one derivatives <b>7a</b>–<b>7d</b>, <b>8a</b>–<b>8d</b>, and <b>9a</b>–<b>9d</b> via reactions with sodium hydroxide, sulfuric acid, and hydrazine hydrate, respectively. The synthesized compounds were screened against Gram-positive and Gram-negative bacteria and fungal strains. Compounds <b>7b</b>, <b>7d</b>, and <b>9b</b> showed high activity against <i>Bacillus subtilis</i> MTCC 121 at a concentration of lower than 8.0 μM. These compounds were also screened for biofilm inhibition activity against <i>B. subtilis</i> MTCC 121 using erythromycin as standard and were subjected to molecular docking studies toward human NAD[P]H-quinone oxidoreductase.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2454 - 2461"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362049","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 Biological Activity of 4-Amino-1,3,5-triaryl-1H-pyrrol-2(5H)-ones","authors":"M. V. Aleksanyan,&nbsp;G. K. Harutyunyan,&nbsp;H. M. Stepanyan,&nbsp;R. Y. Muradyan,&nbsp;S. P. Gasparyan","doi":"10.1134/S1070428024120121","DOIUrl":"10.1134/S1070428024120121","url":null,"abstract":"<p>A series of 4-amino-1,3,5-triaryl-1<i>H</i>-pyrrol-2(5<i>H</i>)-ones have been synthesized by acylation of aryl­acetonitriles with arylacetyl chlorides, followed by intramolecular cyclization in the presence of potassium hydroxide. The synthesized compounds have been evaluated for their antibacterial and antitumor activities; among them, derivatives containing alkyl and alkoxy groups in the aryl fragments at positions <i>1</i>, <i>3</i>, and <i>5</i> of the pyrrole ring turned out to be the most active.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2393 - 2400"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362001","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":"Mass Spectra of New Heterocycles: XXVIII. Electron Impact and Chemical Ionization Mass Spectra of 3- and 5-(1H-Pyrrol-1-yl)- and 3-(1-Methyl-1H-pyrrol-2-yl)thiophen-2-amines","authors":"L. V. Klyba,&nbsp;E. R. Sanzheeva,&nbsp;N. A. Nedolya,&nbsp;O. A. Tarasova","doi":"10.1134/S1070428024120108","DOIUrl":"10.1134/S1070428024120108","url":null,"abstract":"<p>The behavior of previously unknown 3- and 5-(1<i>H</i>-pyrrol-1-yl)- and 3-(1-methyl-1<i>H</i>-pyrrol-2-yl)thiophen-2-amines under electron impact (70 eV) and chemical ionization (reactant gas methane) has been studied. The title compounds were synthesized in one pot from lithiated 1-propa-1,2-dien-1-yl-, 1-prop-2-yn-1-yl-, and 1-methyl-2-prop-1-yn-1-yl-1<i>H</i>-pyrroles, isothiocyanates, and methyl iodide. Under electron impact, all compounds formed stable molecular ions (<i>M</i>^+<b>·</b>, <i>I</i>_rel 100%) which underwent fragmentation along two common pathways, C–N bond cleavage in the amine substituent with charge localization on the sulfur atom and generation of [<i>M</i> – R]⁺ ions (first pathway) and [<i>M</i> – Me]⁺ ions (second pathway). An exception was <i>N</i>-butyl-substituted thiophenamine which showed no [<i>M</i> – Me]⁺ ion in the mass spectrum. The stability of these ions depended on the nature of the R substituent. Thus, the [<i>M</i> – R]⁺ ion peak (R = Alk) had the highest intensity (<i>I</i>_rel 28–91%), whereas the [<i>M</i> – R]⁺ ions (R = Ar) were the least abundant (<i>I</i>_rel 3–8%). In contrast, the intensity of the [<i>M</i> – Me]⁺ ion peak in the mass spectra of <i>N</i>-aryl-substituted thiophenamines (<i>I</i>_rel 28–52%) was higher than the intensity of the corresponding ion peak of <i>N</i>-alkyl analogues (<i>I</i>_rel 14–41%), except for <i>N</i>-ethyl-3-(1-methyl-1<i>H</i>-pyrrol-2-yl)thiophen-2-amine, in the spectrum of which the intensity of the [<i>M</i> – Me]⁺ ion peak was 57%. The [<i>M</i> – R]⁺ and [<i>M</i> – Me]⁺ ions derived from all <i>N</i>,<i>N</i>-dimethylthiophen-2-amines had the same <i>m</i>/<i>z</i> value and structure. The third fragmentation pathway was observed only for <i>N</i>-alkylthiophenamines; it involved α-cleavage in the amine substituent with charge localization on the exocyclic nitrogen atom. The fragmentation pathways of ions derived from all thiophenamines studied were proposed on the basis of analysis of tandem mass spectra (MS²). All 3-(1<i>H</i>-pyrrol-1-yl)thiophen-2-amines under chemical ionization with methane as reactant gas easily underwent protonation, charge transfer, and electrophilic addition processes, and the resulting <i>M</i>^+<b>·</b>, [<i>M</i> + H]⁺ and [<i>M</i> + Et]⁺ gave high-intensity peaks in the mass spectra.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2374 - 2387"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024120108.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362012","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}

{"title":"Facile Conversion of Ketene Dithioacetals to Imidazolidines, Oxazolidines, and Thiazolidines in a Deep Eutectic Solvent","authors":"N. S. Singh,&nbsp;R. K. R. Singh,&nbsp;O. M. Singh,&nbsp;L. G. Chanu,&nbsp;L. R. Singh","doi":"10.1134/S107042802410248","DOIUrl":"10.1134/S107042802410248","url":null,"abstract":"<p>An efficient green synthesis of structurally diverse azole heterocycles by treating ketene diethyl dithioacetals with various binucleophiles has been achieved. Deep eutectic solvent (DES) has been used as a reaction medium, and the optimized conditions and recyclability of the DES have been investigated. The title heterocyclic compounds, namely imidazolidines, 1,3-oxazolidines, and 1,3-thiazolidines, could be generated from easily accessible ketene dithioacetals by reacting with ethylene diamine, ethanolamine, and cysteamine, respectively.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2495 - 2503"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361991","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":"Sustainable Synthesis and Antimicrobial Assessment of 1,4-Dihydropyrimido[1,2-a]benzimidazole Derivatives","authors":"D. Katariya,&nbsp;M. Borisagar","doi":"10.1134/S1070428024120224","DOIUrl":"10.1134/S1070428024120224","url":null,"abstract":"<p>The increasing demand for environmentally friendly and efficient methods in chemical synthesis has driven the exploration of green chemistry approaches in medicinal chemistry. This study focuses on the sustainable synthesis of 1,4-dihydropyrimido[1,2-<i>a</i>]benzimidazole derivatives <b>4a</b>–<b>4o</b> which have shown significant potential due to their diverse biological activities, particularly antimicrobial properties. The target compounds were synthesized using PEG-400 as a solvent, which proved to be the most effective. The antimicrobial activities of these derivatives against a range of pathogenic bacterial and fungal strains were evaluated using the broth dilution method. Compounds <b>4a</b>–<b>4o</b> exhibited notable antimicrobial activity, and some of them showed competitive effectiveness compared to standard reference drugs.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2475 - 2482"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362048","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":"Copper Nanoparticles and Copper-Containing Metal–Organic Coordination Polymers in the Catalytic Amination of 2-Halopyridines","authors":"D. A. Leksakov,&nbsp;A. S. Borisova,&nbsp;A. V. Murashkina,&nbsp;D. S. Kuliukhina,&nbsp;A. D. Averin,&nbsp;V. V. Vergun,&nbsp;V. I. Isaeva,&nbsp;E. N. Savelyev,&nbsp;I. A. Novakov,&nbsp;I. P. Beletskaya","doi":"10.1134/S1070428024120029","DOIUrl":"10.1134/S1070428024120029","url":null,"abstract":"<p>The efficiencies of copper-containing metal–organic coordination polymers (Cu-MOFs) and com­mercially available unsupported copper nanoparticles (CuNPs) in the amination of 2-iodopyridine, 2-bromo­pyridine, 2-bromo-5-(trifluoromethyl)pyridine, and 2-bromo-6-(trifluoromethyl)pyridine with <i>n</i>-octylamine and adamantane-containing amines with different steric environments of the amino group have been compared. Under the optimized conditions, the yields of the amination products in the presence of both catalytic systems were generally similar. In the reactions with 2-bromopyridine, increased reactant concentration and the use of 2 equiv of the substrate were necessary to achieve good yields. The presence of a trifluoromethyl group at the 6-position of the pyridine ring improved the yield of the amination products. An increase in steric hindrances at the amino group resulted in an appreciable decrease in the yield under catalysis by Cu-MOFs; however, reactions with such amines were successfully performed in the presence of CuNPs, and CuNPs of the average size 25 nm proved to be superior to bifractional nanoparticles with average sizes of 10 and 80 nm. On the other hand, increased concentration of the reactants in the Cu-MOF-catalyzed amination provided good yields of the target compounds in the absence of a ligand.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2321 - 2330"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024120029.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361919","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}

{"title":"Synthesis and Antimicrobial Potential of Substituted (Z)-5-Benzylidene-1,3-thiazolidine-2,4-diones with 1,3,4-Oxadiazole Functionalities","authors":"D. V. Pathak,&nbsp;H. A. Modi,&nbsp;P. D. Suradiya,&nbsp;D. B. Chhag,&nbsp;H. Narode,&nbsp;A. K. Mahida,&nbsp;G. L. Jadav","doi":"10.1134/S1070428024120133","DOIUrl":"10.1134/S1070428024120133","url":null,"abstract":"<p>A variety of antimicrobials with distinct modes of action is vital for tackling the challenges associated with multidrug resistance. Herein, we have designed and synthesized novel thiazolidine-2,4-dione derivatives. These scaffolds have been analyzed for their potential antibacterial and antifungal activities. Among all, compound <b>6j</b> exhibited excellent antibacterial activity with inhibition zone diameters ranging from 19 to 24 mm against pathogenic strains <i>Staphylococcus aureus</i>, <i>Streptococcus pyogenes</i>, <i>Escherichia coli</i>, and <i>Pseudomonas aeruginosa</i>. Compounds <b>6a</b> and <b>6g</b> showed moderate antifungal activity with inhibition zone diameters of 24 and 23 mm, respectively, against <i>Aspergillus niger</i> compared to the standard drug Nystatin. Furthermore, the molecular binding affinities of the synthesized thiazolidine-2,4-dione derivatives with proteins from various microorganisms have been assayed by molecular docking studies.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2401 - 2410"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361997","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 the C1–C9 Block of Epothilone D Analogue","authors":"G. R. Sunagatullina,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428024120091","DOIUrl":"10.1134/S1070428024120091","url":null,"abstract":"<p>(2<i>R</i>,5<i>R</i>,6<i>S</i>,7<i>S</i>,9<i>E</i>)-2-{[<i>tert</i>-Butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-4-oxo-6-[(triethylsilyl)oxy]undec-9-enoic acid has been synthesized as the C¹–C⁹ block necessary for the subsequent incorporation into the structure of a desired epothilone D analogue.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2367 - 2373"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362000","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}