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Synthesis of New 1,3a,6,6a-Tetraazapentalene Derivatives under Cadogan Reaction Conditions Cadogan反应条件下新1,3a,6,6a-四氮杂二烯衍生物的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025601761
P. S. Gribanov, A. N. Philippova, M. A. Topchiy, A. F. Smol’yakov, D. V. Vorobyeva, A. N. Rodionov, A. F. Asachenko, S. N. Osipov
{"title":"Synthesis of New 1,3a,6,6a-Tetraazapentalene Derivatives under Cadogan Reaction Conditions","authors":"P. S. Gribanov,&nbsp;A. N. Philippova,&nbsp;M. A. Topchiy,&nbsp;A. F. Smol’yakov,&nbsp;D. V. Vorobyeva,&nbsp;A. N. Rodionov,&nbsp;A. F. Asachenko,&nbsp;S. N. Osipov","doi":"10.1134/S1070428025601761","DOIUrl":"10.1134/S1070428025601761","url":null,"abstract":"<p>A convenient synthetic approach has been developed for novel monobenzotriazoles incorporating a mesoionic 1,3a,6,6a-tetraazapentalene core. The method involves a Cu(I)-catalyzed (3+2) cycloaddition of ortho-nitrophenyl azide to terminal aryl(alkyl)acetylenes, followed by an intramolecular cyclization under Cadogan-type deoxygenation conditions. The process can be successfully performed in a one-pot fashion, affording the target benzo[<i>d</i>][1,2,3]triazolo[1,2-<i>a</i>]triazole derivatives in good yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1034 - 1042"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164456","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
Indole-2-Carboxamide Derivatives: Synthesis and Estimation of Their Potential as Metallo-Beta-Lactamase Inhibitors 吲哚-2-羧酰胺衍生物：合成及其作为金属- β -内酰胺酶抑制剂的潜力的评价
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602511
Р. Tiuleanu, I. V. Ivanov, S. E. Solov’eva, I. P. Andreeva, V. G. Grigorenko, A. M. Egorov, A. E. Shchekotikhin
{"title":"Indole-2-Carboxamide Derivatives: Synthesis and Estimation of Their Potential as Metallo-Beta-Lactamase Inhibitors","authors":"Р. Tiuleanu,&nbsp;I. V. Ivanov,&nbsp;S. E. Solov’eva,&nbsp;I. P. Andreeva,&nbsp;V. G. Grigorenko,&nbsp;A. M. Egorov,&nbsp;A. E. Shchekotikhin","doi":"10.1134/S1070428025602511","DOIUrl":"10.1134/S1070428025602511","url":null,"abstract":"<p>Bacterial resistance to β-lactam antibiotics is one of the key challenges in global healthcare. A major mechanism underlying this resistance is the production of β-lactamases by pathogens. These enzymes are classified into four groups (A–D), with class B metallo-β-lactamases, particularly the NDM family, posing the highest threat. These zinc-dependent enzymes are capable of inactivating nearly all β-lactam antibiotics, and to date, there are no clinically approved inhibitors for this class. Previous studies have shown that certain derivatives of indole-2-carboxylic acid, hydroxamic acids, and glycine-based compounds can inhibit NDM-1 by interacting with Zn<sup>2+</sup> ions and amino acid residues within the enzyme’s active site. However, the antibacterial potential of indole-2-carboxamide derivatives of the aforementioned compounds has not yet been explored as inhibitors of metallo-β-lactamases. In the search for new candidates to develop specific metallo-β-lactamase inhibitors, a known indole-2-carboxylic acid-based NDM-1 inhibitor was modified to prepared previously undescribed analogues—indole-2-carboxamides bearing fragments derived from hydroxamic acid, glycine, and iminodiacetic acid. To accomplish this, a method commonly used in peptide synthesis was adapted, employing the condensing agent PyBOP. The resulting compounds demonstrated the ability to inhibit NDM-1 in the micromolar concentration range (IC<sub>50</sub> = 20–60 µM), highlighting the significant role of the substituent at position 2 in binding to the enzyme’s active site. It was shown that modifying the carboxyl group at position 2 of the indole core with functional fragments possessing intrinsic inhibitory activity leads to a reduction in the activity of the parent indole-2-carboxylic acid derivative.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1134 - 1140"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164458","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 Spacered Disaccharides Structurally Related to the Fucosylated Chondroitin Sulfates from Sea Cucumbers Holothuria nobilis and Psolus peronii 与海参和海参聚焦硫酸软骨素相关的间隔双糖的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602304
Z. V. Serpokrylov, D. V. Yashunsky, E. V. Sukhova, V. B. Krylov, N. E. Nifantiev
{"title":"Synthesis of Spacered Disaccharides Structurally Related to the Fucosylated Chondroitin Sulfates from Sea Cucumbers Holothuria nobilis and Psolus peronii","authors":"Z. V. Serpokrylov,&nbsp;D. V. Yashunsky,&nbsp;E. V. Sukhova,&nbsp;V. B. Krylov,&nbsp;N. E. Nifantiev","doi":"10.1134/S1070428025602304","DOIUrl":"10.1134/S1070428025602304","url":null,"abstract":"<p>The synthesis of selectively 3,4′,6′-tri- and 3,4,4′,6′-tetra-<i>O</i>-sulfated derivatives of the aminopropyl glycoside of the disaccharide α-D-GalNAc-(1→2)-α-L-Fuc (<b>1</b> and <b>2</b>), structurally related to highly unusual carbohydrate chain fragments of hexosaminoglycans found in the side chains of fucosylated chondroitin sulfates (FCS) from sea cucumbers <i>Holothuria nobilis</i> and <i>Psolus peronii</i>, is described. Spacered disaccharides <b>1</b> and <b>2</b> were obtained via a common synthetic route involving selectively protected L-fucose and phenyl-1-seleno-2-azido-2-deoxygalactose building blocks, the latter synthesized by azidophenylselenylation of triacetylgalactal. Target compounds <b>1</b> and <b>2</b> will be used as model structures to identify the pharmacophoric elements within these FCS that are responsible for their biological activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1043 - 1055"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165550","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 Conjugates of N-(Purin-6-yl)-6-aminohexanoic Acid with 4-Amino-1-aryl-5-oxoprolines N-（嘌呤-6-基）-6-氨基己酸与4-氨基-1-芳基-5-氧脯氨酸缀合物的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602444
A. Yu. Vigorov, O. A. Vozdvizhenskaya, A. A. Tumashov, T. V. Matveeva, I. N. Ganebnykh, G. L. Levit, V. P. Krasnov
{"title":"Synthesis of Conjugates of N-(Purin-6-yl)-6-aminohexanoic Acid with 4-Amino-1-aryl-5-oxoprolines","authors":"A. Yu. Vigorov,&nbsp;O. A. Vozdvizhenskaya,&nbsp;A. A. Tumashov,&nbsp;T. V. Matveeva,&nbsp;I. N. Ganebnykh,&nbsp;G. L. Levit,&nbsp;V. P. Krasnov","doi":"10.1134/S1070428025602444","DOIUrl":"10.1134/S1070428025602444","url":null,"abstract":"<p>(2<i>S</i>,4<i>S</i>)-4-Amino-1-aryl-5-oxoprolines were synthesized by nucleophilic substitution of the bromine atom in dimethyl (2<i>S</i>,4<i>RS</i>)-4-bromo-<i>N</i>-phthaloylglutamate under the action of difluorosubstituted anilines followed by isolation of (2<i>S</i>,4<i>S</i>)-diastereomers and removal of protecting groups; subsequent coupling of their methyl esters with <i>N</i>-(purin-6-yl)-6-aminohexanoic acid and saponification of ester groups led to the formation of target conjugates. The saponification of ester groups was accompanied by minor epimerization.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1089 - 1098"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165598","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
Dear Valentin Pavlovich, Dear Valya! 亲爱的瓦伦丁·帕夫洛维奇，亲爱的瓦莉亚！
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025060028
Irina Beletskaya, Mikhail Egorov, Alexander Terentyev
{"title":"Dear Valentin Pavlovich, Dear Valya!","authors":"Irina Beletskaya, Mikhail Egorov, Alexander Terentyev","doi":"10.1134/S1070428025060028","DOIUrl":"10.1134/S1070428025060028","url":null,"abstract":"","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"983 - 983"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164459","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 2,4-Disubstituted Quinolines by the Reaction of Propargylic Alcohols with Anilines in a Polyphosphoric Acid Medium 丙炔醇与苯胺在多磷酸介质中反应合成2,4-二取代喹啉
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602687
A. V. Aksenov, N. A. Aksenov, A. S. Akulova, D. C. Makieva, I. V. Aksenova, N. A. Arutiunov, D. A. Aksenov
{"title":"Synthesis of 2,4-Disubstituted Quinolines by the Reaction of Propargylic Alcohols with Anilines in a Polyphosphoric Acid Medium","authors":"A. V. Aksenov,&nbsp;N. A. Aksenov,&nbsp;A. S. Akulova,&nbsp;D. C. Makieva,&nbsp;I. V. Aksenova,&nbsp;N. A. Arutiunov,&nbsp;D. A. Aksenov","doi":"10.1134/S1070428025602687","DOIUrl":"10.1134/S1070428025602687","url":null,"abstract":"<p>A novel method for quinoline synthesis based on the interaction of propargylic alcohols with anilines in the presence of polyphosphoric acid (PPA) has been developed. It has been discovered that propargylic alcohols in a PPA medium are capable of hydrolyzing into chalcones. The use of PPA in ethyl acetate solution has been demonstrated for the first time.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1141 - 1147"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164452","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
1,2,5-Telluradiazoloporphyrazines: III. Detelluration of 1,2,5-Telluradiazolo­tribenzoporphyrazine and Its Conversion to Pyrazine-Fused Bis-phthalocyanine 1、2、5-Telluradiazoloporphyrazines: III。1,2,5-碲二唑-三苯并卟啉的脱水及转化为吡嗪-融合双酞菁
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S107042802506003X
M. S. Mikhailov, S. S. Ivanova, P. A. Stuzhin
{"title":"1,2,5-Telluradiazoloporphyrazines: III. Detelluration of 1,2,5-Telluradiazolo­tribenzoporphyrazine and Its Conversion to Pyrazine-Fused Bis-phthalocyanine","authors":"M. S. Mikhailov,&nbsp;S. S. Ivanova,&nbsp;P. A. Stuzhin","doi":"10.1134/S107042802506003X","DOIUrl":"10.1134/S107042802506003X","url":null,"abstract":"<p>Treatment of Mg<sup>II</sup> complex of <i>tert</i>-butyl substituted 1,2,5-telluradiazolotribenzoporphyrazine with acetic or trifluoroacetic acid leads, along with the demetallation of the macrocycle, to the expulsion of the Te atom and formation of diimino- and dioxoporphyrazines. Detelluration upon treatment with CF<sub>3</sub>COOH in pyridine solution results in dimerization affording planar bisphthalocyanines with the bridge pyrazine moiety</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1172 - 1179"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164455","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
A Comparison of Catalytic Activity of Ammonium and Phosphonium Salts in Carboxylation of Epoxides without Lewis Acids 不含路易斯酸的环氧化合物羧化反应中铵盐和磷酸盐催化活性的比较
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1134/S1070428025602274
N. Yu. Kuznetsov, S. E. Lyubimov, P. V. Cherkasova, I. P. Beletskaya
{"title":"A Comparison of Catalytic Activity of Ammonium and Phosphonium Salts in Carboxylation of Epoxides without Lewis Acids","authors":"N. Yu. Kuznetsov,&nbsp;S. E. Lyubimov,&nbsp;P. V. Cherkasova,&nbsp;I. P. Beletskaya","doi":"10.1134/S1070428025602274","DOIUrl":"10.1134/S1070428025602274","url":null,"abstract":"<p>A comparative analysis was performed to evaluate the catalytic efficiency of various organocatalysts for the carboxylation of epoxides based on ammonium and phosphonium salts. The results show that for low molecular weight onium salts, the efficiency of epoxide carboxylation depends on both the catalyst structure and its solubility in the reaction medium. The highest efficiency was achieved with tetrabutyl-substituted onium iodides and bromides. The addition of 20 mol % water together with the onium salt significantly accelerates the reaction with epoxides and results in quantitative yields of mono- and disubstituted cyclic carbonates. A polystyrene-based catalyst modified with an immobilized tributylphosphonium group (4 mol %) combined with 1 eq. of water produces a quantitative yield of butylene carbonate and can be reused without loss of catalytic activity (tested over 10 cycles), making it promising for practical applications.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 6","pages":"1066 - 1075"},"PeriodicalIF":0.9,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164457","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
Dibenzoylmethane in the Synthesis of Selenium Di- and Tetrahydropyridine-3-carbonitriles 二苯甲酰甲烷在二硒和四氢吡啶-3-碳腈合成中的应用
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567825601111
K. A. Frolov, B. S. Krivokolysko, N. А. Aksenov, S. G. Krivokolysko
{"title":"Dibenzoylmethane in the Synthesis of Selenium Di- and Tetrahydropyridine-3-carbonitriles","authors":"K. A. Frolov,&nbsp;B. S. Krivokolysko,&nbsp;N. А. Aksenov,&nbsp;S. G. Krivokolysko","doi":"10.1134/S1234567825601111","DOIUrl":"10.1134/S1234567825601111","url":null,"abstract":"<p>3-Cyano-6-hydroxy-1,4,5,6-tetrahydropyridine-2-ammonium selenolates have been synthesized by the reaction of cyanoselenoacetamide, furan-2- or thiophene-2-carbaldehyde, and dibenzoylmethane in ethanol in the presence of an excess of piperidine or morpholine under argon and then used to obtain 2-alkylselenodi- and tetrahydropyridine-3-carbonitriles. The structures of the latter products were analyzed by X-ray diffraction.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"826 - 830"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143157","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 Antioxidant Activity Evaluation of Novel 1,3,5-Triazine Derivatives Bearing a 4-(4-Aminophenyl)morpholin-3-one Moiety 含有4-（4-氨基苯基）morpholin-3-one片段的新型1,3,5-三嗪衍生物的合成及抗氧化活性评价
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824604522
Krishna Limbasiya, Jayesh Babariya, Khushal Kapadiya, Vasta Modhavadiya
{"title":"Synthesis and Antioxidant Activity Evaluation of Novel 1,3,5-Triazine Derivatives Bearing a 4-(4-Aminophenyl)morpholin-3-one Moiety","authors":"Krishna Limbasiya,&nbsp;Jayesh Babariya,&nbsp;Khushal Kapadiya,&nbsp;Vasta Modhavadiya","doi":"10.1134/S1234567824604522","DOIUrl":"10.1134/S1234567824604522","url":null,"abstract":"<p>A series of novel 1,3,5-triazine 4-(4-aminophenyl)morpholin-3-one derivatives were synthesized in two stages. First, the nitrogen-ring 1,3,5-triazine was reacted with 4-(4-aminophenyl)morpholin-3-one to obtain 4-{4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]phenyl}morpholin-3-one via C<sup>2</sup>–N coupling under mild basic conditions at a low temperature (K<sub>2</sub>CO<sub>3</sub>, 0°C). The subsequent C–O couplings of the product at the C<sup>4</sup> and C<sup>6</sup> positions with various phenols were performed under reflux in the presence of K<sub>2</sub>CO<sub>3</sub> to yield the target 4-(4-{[4,6-bis(substituted phenoxy)-1,3,5-triazin-2-yl]amino}phenyl)morpholin-3-ones. All the synthesized compounds were characterized by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry. The products were tested for antioxidant activity by the DPPH assay using ascorbic acid as reference drug (IC<sub>50</sub> = 350.01 ± 3.07 µM). It was found that the derivatives with electron-donor substituents in the phenoxy group (3-Me, 4-Me, and 4-Et<b>)</b> exhibited a notable antioxidant effect (IC<sub>50</sub> ≈ 210 µM), with the highest potency of them demonstrated by the 4-ethyl derivative (IC<sub>50</sub> = 190.55 ± 0.94 µM).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"951 - 957"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143159","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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