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Russian Journal of Organic Chemistry最新文献

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Synthesis and Neurotropic Activity of Cyclic and Spirocyclic Derivatives of 1,3-Diazadamantane 1,3-重氮金刚烷环和螺环衍生物的合成及其嗜神经活性
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567825601330
M. V. Galstyan, A. D. Harutyunyan, K. A. Gevorkyan, M. V. Aleksanyan, I. M. Nazaryan, R. G. Paronikyan, S. P. Gasparyan
{"title":"Synthesis and Neurotropic Activity of Cyclic and Spirocyclic Derivatives of 1,3-Diazadamantane","authors":"M. V. Galstyan,&nbsp;A. D. Harutyunyan,&nbsp;K. A. Gevorkyan,&nbsp;M. V. Aleksanyan,&nbsp;I. M. Nazaryan,&nbsp;R. G. Paronikyan,&nbsp;S. P. Gasparyan","doi":"10.1134/S1234567825601330","DOIUrl":"10.1134/S1234567825601330","url":null,"abstract":"<p>Cyclic and spirocyclic 1,3-diazaadamantane derivatives were synthesized by the condensation of substituted 3,7-diazabicyclo[3.3.1]nonanes with cyclic and heterocyclic aldehydes and ketones. Screening for neurotropic activity showed that spirocyclic 1,3-diazaadamantanes exhibit a higher potency than their cyclic analogs, with activity levels of 40–60 against 20–40%, respectively.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"864 - 871"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143164","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
Intramolecular Cyclization of Grignard or Blaise Intermediates for the Synthesis of a Chiral Piperidine-2,4-dione Derived from (R)-(‒)-Phenylglycinol (R)-(-)-苯甘二醇手性哌啶-2,4-二酮分子内环化研究
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824604194
H. Rodríguez-Matsui, A. Aguilar-Aguilar, A. Carrasco-Carballo, V. Carranza-Téllez, A. Palillero-Cisneros, J. R. Juárez Posadas, J. L. Terán, D. M. Aparicio
{"title":"Intramolecular Cyclization of Grignard or Blaise Intermediates for the Synthesis of a Chiral Piperidine-2,4-dione Derived from (R)-(‒)-Phenylglycinol","authors":"H. Rodríguez-Matsui,&nbsp;A. Aguilar-Aguilar,&nbsp;A. Carrasco-Carballo,&nbsp;V. Carranza-Téllez,&nbsp;A. Palillero-Cisneros,&nbsp;J. R. Juárez Posadas,&nbsp;J. L. Terán,&nbsp;D. M. Aparicio","doi":"10.1134/S1234567824604194","DOIUrl":"10.1134/S1234567824604194","url":null,"abstract":"<p>In this work, we describe the synthesis of chiral (<i>R</i>)-(‒)-piperidine-2,4-dione derived from (<i>R</i>)-(‒)-phenylglycinol, a valuable building block for the diastereoselective synthesis of piperidine alkaloids. The key step involves intramolecular cyclization: when the electrophile is an ester, the reaction proceeds via the formation of a Grignard intermediate, whereas when the electrophile is a nitrile, the cyclization follows a Blaise-type mechanism.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"911 - 918"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143277","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
Water-Soluble Calix[4]resorcinarenes with Amino Acid Moieties at the Upper Rim: Synthesis, Characterization, and Properties 上缘氨基酸部分的水溶性杯状间苯二甲酸脂：合成、表征和性质
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824604777
Jing-Long Liu, Xin-Min Zhou, Lu-Si Chen, Ai-Quan Jia, Qian-Feng Zhang
{"title":"Water-Soluble Calix[4]resorcinarenes with Amino Acid Moieties at the Upper Rim: Synthesis, Characterization, and Properties","authors":"Jing-Long Liu,&nbsp;Xin-Min Zhou,&nbsp;Lu-Si Chen,&nbsp;Ai-Quan Jia,&nbsp;Qian-Feng Zhang","doi":"10.1134/S1234567824604777","DOIUrl":"10.1134/S1234567824604777","url":null,"abstract":"<p>A series of amino acid-functionalized calix[4]resorcinarenes was synthesized via a Mannich reaction involving four calix[4]resorcinarenes bearing ethyl, propyl, <i>iso</i>-butyl, or benzyl substituents at the lower rim, five amino acids (both chiral and achiral), and aqueous formaldehyde (37%). The structures of the synthesized compounds were confirmed by IR and NMR spectroscopy and ESI mass spectrometry. The water solubility of the products significantly enhanced compared to that of the parent calix[4]resorcinarenes. This is especially true of the synthesized calix[4]resorcinarenes bearing <i>N</i>-methyl-L-alanine moieties: at room temperature, the pH of aqueous solutions of these compounds was lower by more than 2.0 units compared to their respective precursors. In contrast, the parent benzyl-substituted calix[4]resorcinarenes and its amino acid derivatives showed a relatively low water solubility. Notably, the L-proline calix[4]resorcinarene derivative with <i>iso</i>-butyl substituents at the lower rim demonstrated potential for application in asymmetric catalysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"919 - 930"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143309","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
Catalytic Rearrangement of a Tetrasubstituted Tetrahydropyridine 四取代四氢吡啶的催化重排
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567825601214
F. N. Naghiyev, M. R. Komarovskikh, M. V. Tachaev, V. N. Khrustalev, I. G. Mamedov
{"title":"Catalytic Rearrangement of a Tetrasubstituted Tetrahydropyridine","authors":"F. N. Naghiyev,&nbsp;M. R. Komarovskikh,&nbsp;M. V. Tachaev,&nbsp;V. N. Khrustalev,&nbsp;I. G. Mamedov","doi":"10.1134/S1234567825601214","DOIUrl":"10.1134/S1234567825601214","url":null,"abstract":"<p>A new compound, 5-acetyl-2-amino-4-(2-chloro-5-nitrophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile, was synthesized by the reaction of 2-chloro-5-(nitrobenzylidene)malononitrile with malononitrile and aniline. The product was then subjected to catalytic rearrangement in the presence of ethylenediamine to obtain one more new compound, 4-(2-chloro-5-nitrophenyl)-6-oxo-2-(phenylamino)-1,4,5,6-tetrahydropyridine-3-carbonitrile. The structure of the products was confirmed by NMR spectroscopy and X-ray diffraction analysis. A plausible mechanism of the rearrangement reaction was proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"821 - 825"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143152","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 Novel Amino Derivatives of 1,3-Diaza- and 1,3,5-Triazadamantanes 1,3-二氮杂烷和1,3,5-三氮杂烷新型氨基衍生物的合成
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824601311
K. A. Gevorkyan, M. V. Galstyan, M. V. Aleksanyan, J. A. Avakimyan, H. M. Stepanyan, R. Y. Muradyan, A. D. Harutyunyan
{"title":"Synthesis of Novel Amino Derivatives of 1,3-Diaza- and 1,3,5-Triazadamantanes","authors":"K. A. Gevorkyan,&nbsp;M. V. Galstyan,&nbsp;M. V. Aleksanyan,&nbsp;J. A. Avakimyan,&nbsp;H. M. Stepanyan,&nbsp;R. Y. Muradyan,&nbsp;A. D. Harutyunyan","doi":"10.1134/S1234567824601311","DOIUrl":"10.1134/S1234567824601311","url":null,"abstract":"<p>A number of novel diaza- and triazaadamantane derivatives were synthesized by the reactions of 5,7-disubstituted 2-(4-aminophenyl)-1,3-diazaadamantanes, 1,3,5-triazaadamantane-7-amine, and (aminophenyl)(1,3,5-triazaadamantan-7-yl))methanones with anhydrides of substituted succinic and glutaric acids. Some of the synthesized compounds showed a moderate antibacterial activity against both Gram-positive and Gram-negative bacteria.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"847 - 854"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145142916","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
Biological Evaluation and Molecular Docking Study of (E)-N-(2-Aminophenyl)-3-(quinolin-4-yl)acrylamides as Potential Anticolon Cancer Agents (E)- n-（2-氨基苯基）-3-（喹啉-4-基）丙烯酰胺作为潜在抗结肠癌药物的生物学评价及分子对接研究
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824603966
S. S. Gagare, V. P. Choudhari, A. S. Jain, S. N. Mali
{"title":"Biological Evaluation and Molecular Docking Study of (E)-N-(2-Aminophenyl)-3-(quinolin-4-yl)acrylamides as Potential Anticolon Cancer Agents","authors":"S. S. Gagare,&nbsp;V. P. Choudhari,&nbsp;A. S. Jain,&nbsp;S. N. Mali","doi":"10.1134/S1234567824603966","DOIUrl":"10.1134/S1234567824603966","url":null,"abstract":"<p>This study reports evaluation of the earlier reported series of (<i>E</i>)-<i>N</i>-(2-aminophenyl)-3-(quinolin-4-yl)acrylamides as potential inhibitors of histone deacetylase 8 (HDAC8) with anti-colon cancer activities. The target compounds were synthesized via four-step procedure, starting with quinoline-4-carboxylic acid derivatives. All synthesized molecules were tested for HDAC8 inhibitory activity using in vitro enzymatic assays, and their antiproliferative effects were evaluated against HCT-116 and COLO 205 colon cancer cell lines using the MTT assay. Among the tested compounds, (2<i>E</i>)-<i>N</i>-(2-aminophenyl)-3-(2-phenylquinolin-4-yl)prop-2-enamide (<b>A</b>) was found to be the most potent HDAC8 inhibitor with an IC<sub>50</sub> of 4.23 µM, and compound <b>(</b>2<i>E</i>)-<i>N</i>-(2-Aminophenyl)-3-(3-ethyl-2-phenylquinolin-4-yl)prop-2-enamide was the least active (IC<sub>50</sub> = 23.43 µM). In terms of the antiproliferative activity, compound <b>A</b> again showed the strongest effect on HCT-116 cells (EC<sub>50</sub> 17.42 µM), whereas (2<i>E</i>)-<i>N</i>-(2-aminophenyl)-3-(2,3-dimethyl-6-nitroquinolin-4-yl)prop-2-enamide demonstrated significant efficacy against COLO 205 cells (EC<sub>50</sub> 12.77 µM). The molecular docking study using the crystal structure of HDAC8 (PDB ID: 1T69) provided evidence for the favourable binding interactions of compounds in the enzyme active site. These findings suggest that quinoline derivatives, particularly compound <b>A</b> represent promising lead scaffolds for the development of HDAC8-targeted anticolon cancer therapeutics.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"902 - 910"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143160","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
Synthetic Approaches to Heterocyclic Scaffolds: 4-Thiazolidinone Derivatives as Heterocyclic Scaffolds: Synthesis and Biological Activity (A Review) 杂环支架的合成方法：4-噻唑烷酮衍生物杂环支架的合成及生物活性综述
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824604856
Jay Thakkar, Hasit Vaghani, Hit Kardani, Prachi Patel
{"title":"Synthetic Approaches to Heterocyclic Scaffolds: 4-Thiazolidinone Derivatives as Heterocyclic Scaffolds: Synthesis and Biological Activity (A Review)","authors":"Jay Thakkar,&nbsp;Hasit Vaghani,&nbsp;Hit Kardani,&nbsp;Prachi Patel","doi":"10.1134/S1234567824604856","DOIUrl":"10.1134/S1234567824604856","url":null,"abstract":"<p>A comprehensive review of the authors’ research focused on the development of novel and efficient synthetic strategies for structurally diverse heterocyclic scaffolds is presented. Among these, the thiazolidinone scaffold has emerged as highly versatile and pharmaceutically significant framework in modern medicinal chemistry, owing to its broad clinical relevance. The review covers the recent literature on the design and synthesis of diverse 1,3-thiazolidin-4-one derivatives and investigation of their biological properties and highlights the tremendous potential of thiazolidinones in advancing organic and medicinal chemistry.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"765 - 799"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143247","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 N-Benzoxyamine-derived Tertiary Amines from Hydroxylamine via the Nucleophilic Addition Reaction 亲核加成反应由羟胺合成n -苯并氧胺衍生物叔胺
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567825600865
Mengnan Tong
{"title":"Synthesis of N-Benzoxyamine-derived Tertiary Amines from Hydroxylamine via the Nucleophilic Addition Reaction","authors":"Mengnan Tong","doi":"10.1134/S1234567825600865","DOIUrl":"10.1134/S1234567825600865","url":null,"abstract":"<p>A versatile, convenient, mild, and efficient method for the synthesis of N-benzoyloxyamines containing alkenone or allyl ester groups, starting from hydroxylamine derivatives, is developed and successfully extended to a broader range of tertiary amine analogs.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"872 - 880"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143161","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, Spectral Identification, and Antibacterial Activity of New Schiff Base Curcumin Derivatives 新型希夫碱姜黄素衍生物的合成、光谱鉴定及抗菌活性研究
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567823602206
I. A. A. Hamdan, R. A. A. Aljabawi, W. A. Mahdi, A. A. AlHasan Hamdan
{"title":"Synthesis, Spectral Identification, and Antibacterial Activity of New Schiff Base Curcumin Derivatives","authors":"I. A. A. Hamdan,&nbsp;R. A. A. Aljabawi,&nbsp;W. A. Mahdi,&nbsp;A. A. AlHasan Hamdan","doi":"10.1134/S1234567823602206","DOIUrl":"10.1134/S1234567823602206","url":null,"abstract":"<p>This work describes the synthesis of new Schiff bases that link curcumin with five third-generation cephalosporin antibiotics (cefotaxime, ceftazidime, ceftriaxone, cefixime, and cefdinir), using both mono- and bis-substituted curcumin derivatives. The synthesized compounds were characterized by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and elemental analysis. Their bioactivity was evaluated against <i>S. aureus</i>, <i>P. aeruginosa</i>, and <i>E. coli</i>. Molecular docking was performed to assess the binding affinities of the products to the penicillin-binding proteins PBP1a, PBP1b, PBP4, and PBP6, using some of the synthesized curcumin-derivatives as representative examples. Toxicity prediction indicated potential immunotoxicity, with estimated median lethal doses (LD<sub>50</sub>) ranging from 1000 to 800 mg/kg.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"892 - 901"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143165","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
Green Synthesis of Isoxazole Derivatives by a One-Pot Multicomponent Reaction and Their Antiviral Activity Evaluation 一锅多组分绿色合成异恶唑衍生物及其抗病毒活性评价
IF 0.9 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1134/S1234567824604765
A. Kaur, S. Sharma, A. Sharma, D. Utreja, M. Aggarwal
{"title":"Green Synthesis of Isoxazole Derivatives by a One-Pot Multicomponent Reaction and Their Antiviral Activity Evaluation","authors":"A. Kaur,&nbsp;S. Sharma,&nbsp;A. Sharma,&nbsp;D. Utreja,&nbsp;M. Aggarwal","doi":"10.1134/S1234567824604765","DOIUrl":"10.1134/S1234567824604765","url":null,"abstract":"<p>A series of 4-substituted isoxazole derivatives were synthesized by a one-pot multicomponent reaction between aromatic aldehydes, ethyl acetoacetate, and hydroxylamine hydrochloride, with sulfonated rice straw ash (RSA-SO<sub>3</sub>H) used as an acid catalyst. The synthesized compounds were characterized using IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry. The antiviral activities of these derivatives were evaluated in vivo on <i>Kufri Jyoti</i> potato plants against the mechanically transmitted ssRNA Potato Virus Y (PVY), employing protective, simultaneous, and curative treatment approaches. Among the synthesized compounds, (4-(4-diethylamino)benzylidene)-3-methylisoxazol-5(4<i>H</i>)-one exhibited a significant antiviral activity, particularly in the protective treatment at a concentration of 250 µg/mL.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 5","pages":"941 - 950"},"PeriodicalIF":0.9,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145143276","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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