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Russian Journal of Organic Chemistry最新文献

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Green Synthesis of Bisindolylmethane Derivatives (A Review) 双吲哚基甲烷衍生物的绿色合成（综述）
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-01-11 DOI: 10.1134/S1070428024130025
Hala Bakr El-Nassan
{"title":"Green Synthesis of Bisindolylmethane Derivatives (A Review)","authors":"Hala Bakr El-Nassan","doi":"10.1134/S1070428024130025","DOIUrl":"10.1134/S1070428024130025","url":null,"abstract":"<p>Bisindolylmethane (BIM) derivatives represent an effective class of biologically active compounds. BIM derivatives were reported to exhibit antimicrobial, anticancer, antioxidant effects and many other pharmacological activities. This initiated the need for more effective, simple and rapid methods for their synthesis. Many of these methods are considered as green synthetic methods. The present review highlighted the most important methods reported for the synthesis of BIMs in the last 20 years with a special focus on the work published in the last five years.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S9 - S21"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941273","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
Microwave-Assisted Synthesis and Characterization of Calix[4]resorcinarenes 杯萼[4]间苯二甲酸酯的微波辅助合成与表征
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S107042802410018X
P. H. Kanaiya, V. K. Jain
{"title":"Microwave-Assisted Synthesis and Characterization of Calix[4]resorcinarenes","authors":"P. H. Kanaiya,&nbsp;V. K. Jain","doi":"10.1134/S107042802410018X","DOIUrl":"10.1134/S107042802410018X","url":null,"abstract":"<p>Microwave irradiation was used to promote the cyclocondensation of certain aldehydes and resorcinol, resulting in a sustainable synthesis of calix[4]resorcinarenes. This environmentally conscious technology possesses numerous attractive characteristics, including high productivity, short reaction time, and straightforward workup protocol. The structures of all calix[4]resorcinarenes were verified using a range of physicochemical techniques, including elemental analysis, FT-IR, <sup>1</sup>H NMR, and mass spectrometry.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2014 - 2019"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858722","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, Crystal Structure, and Antibacterial Activity of N-(2-Chlorobenzyl)-3-methylbut-2-enamide N-（2-氯苯基）-3-甲基丁-2-氨基酰胺的合成、晶体结构及抗菌活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100191
W. J. Hu, Y. Q. Liu, J. Y. Yu
{"title":"Synthesis, Crystal Structure, and Antibacterial Activity of N-(2-Chlorobenzyl)-3-methylbut-2-enamide","authors":"W. J. Hu,&nbsp;Y. Q. Liu,&nbsp;J. Y. Yu","doi":"10.1134/S1070428024100191","DOIUrl":"10.1134/S1070428024100191","url":null,"abstract":"<p><i>N</i>-(2-Сhlorobenzyl)-3-methylbut-2-enamide was synthesized, and its structure was determined by single crystal X-ray diffraction and other spectroscopic methods. The compound crystallized in <i>P</i>-1 space group of the triclinic crystal system with the following unit cell parameters: <i>a</i> = 8.8767(5), <i>b</i> = 10.2535(6), <i>c</i> = 13.8768(7) Å; α = 98.608(4)°, β = 103.920(4)°, γ = 98.298(4)°; <i>Z</i> = 4; <i>d</i><sub>calc</sub> = 1.248 g/cm<sup>3</sup>; <i>V</i> = 1190.54(12) Å<sup>3</sup>. Preliminary antibacterial tests showed that <i>N</i>-(2-chlorobenzyl)-3-methylbut-2-enamide exhibited strong antibacterial activity against <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> with minimum inhibitory concentration (MIC) values of 0.01 and 0.02 g/mL, respectively. However, this compound has no obvious bacteriostatic effect on <i>Enterobacter aerogenes</i>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2020 - 2025"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859590","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 Facile and Highly Efficient One-Pot Synthesis of Symmetrical and Unsymmetrical Aldazines Using Reusable MMZHY Solid Acid Catalyst 使用可重复使用的MMZHY固体酸催化剂一锅快速高效合成对称和不对称醛嗪
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100099
S. Ilaamirthamani, M. Kumarraja
{"title":"A Facile and Highly Efficient One-Pot Synthesis of Symmetrical and Unsymmetrical Aldazines Using Reusable MMZHY Solid Acid Catalyst","authors":"S. Ilaamirthamani,&nbsp;M. Kumarraja","doi":"10.1134/S1070428024100099","DOIUrl":"10.1134/S1070428024100099","url":null,"abstract":"<p>A detailed study on one-pot synthesis of 2,3-diaza-1,3-butadiene derivatives from various aromatic aldehydes and hydrazine by using MMZ<sub>HY</sub> solid acid catalyst is reported. The role of the bifunctional nature of MMZ<sub>HY</sub> and the effect of metal ions in the catalyst are described with a supportive mechanism. Both sym­metrical and unsymmetrical aldazines (hydrazone free) were prepared with excellent yields and characterized by <sup>1</sup>H and <sup>13</sup>C NMR spectra. The other advantages of the catalytic system like its easy preparation by the bottom-up method, reusability, multiporous nature which reduces diffusional limitations, easy separation, and mild reaction conditions with higher yield of products are also highlighted.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1950 - 1955"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859705","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 Practical Transition Metal-Free Synthesis of Highly Substituted Thiophenes Containing a Benzoxazole Moiety and Their Antimicrobial Activity 含苯并恶唑高取代噻吩的无过渡金属合成及其抑菌活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100105
A. Hfaiedh, I. Smari, H. Marzouki, Ch. Youssef, H. Ben Ammar
{"title":"A Practical Transition Metal-Free Synthesis of Highly Substituted Thiophenes Containing a Benzoxazole Moiety and Their Antimicrobial Activity","authors":"A. Hfaiedh,&nbsp;I. Smari,&nbsp;H. Marzouki,&nbsp;Ch. Youssef,&nbsp;H. Ben Ammar","doi":"10.1134/S1070428024100105","DOIUrl":"10.1134/S1070428024100105","url":null,"abstract":"<p> Two new series of 3-(pyrrol-1-yl)thiophene derivatives <b>3a</b>–<b>3c</b> and 3-amino-4-(1,3-benzoxazol-2-yl)-5-(substituted-amino)thiophene derivatives <b>5a</b>–<b>5f</b> were synthesized in 75–85% and up to 91% yields, respectively, from readily available and simple substrates. Substrates <b>2a–2c</b> underwent an amino group change into a pyrrole unit on heating in acetic acid. This protocol has been proven effective by a scaled-up reaction and synthetic transformation. The functional group tolerance and substrate scope of this approach were both approved. It was also possible to prepare substituted thiophenes in a single process. The synthesized thiophene derivatives were tested for their antibacterial effects. The results showed that the presence of a ketone group on the thiophene unit was more efficient compared to the ester group. Compounds <b>2c</b>, <b>5b</b>, and <b>5c</b> showed higher antibacterial activity against both Gram-positive and Gram-negative bacteria. Particularly, compound <b>5b</b> exhibited the highest antibacterial activity with a MIC value of 0.0625 mg/mL against <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i> and with a MIC value of 0.125 mg/mL for <i>Bacillus subtilis</i>, <i>Salmonella enterica</i>, and <i>Pseudomonas aeruginosa</i>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1956 - 1962"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859761","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, Identification, and Antibacterial Activity of Thioglycoside Derivatives of 1,3,4-Oxadiazole-2-thiols 1,3,4-恶二唑-2-硫醇的硫代糖苷衍生物的合成、鉴定和抗菌活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100117
S. J. Abed, M. R. Ahmad
{"title":"Synthesis, Identification, and Antibacterial Activity of Thioglycoside Derivatives of 1,3,4-Oxadiazole-2-thiols","authors":"S. J. Abed,&nbsp;M. R. Ahmad","doi":"10.1134/S1070428024100117","DOIUrl":"10.1134/S1070428024100117","url":null,"abstract":"<p>Thioglycoside analogues play an important role in different pharmaceutical products; therefore, we synthesized new thioglycoside analogues containing a 2-sulfanyl-1,3,4-oxadiazole moiety. The main steps of the synthesis were condensation of benzohydrazides with carbon disulfide to form 5-aryl-1,3,4-oxadiazole-2-thiols which were coupled with bromo sugars in the presence of triethylamine to afford the corresponding <i>S</i>-glycoside analogues. The subsequent deprotection of the latter in basic medium gave free thioglycoside derivatives. The structure of all isolated compounds was confirmed by FT-IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. The target products showed good antibacterial activity in vitro.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1963 - 1967"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859762","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 Functionally Substituted 4H-Thiopyrans by Reaction of Carbon Disulfide with Malononitrile Trimer 二硫化碳与丙二腈三聚物反应合成功能取代的 4H-Thiopyrans
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100038
K. V. Lipin, S. A. Blinov, I. N. Bardasov
{"title":"Synthesis of Functionally Substituted 4H-Thiopyrans by Reaction of Carbon Disulfide with Malononitrile Trimer","authors":"K. V. Lipin,&nbsp;S. A. Blinov,&nbsp;I. N. Bardasov","doi":"10.1134/S1070428024100038","DOIUrl":"10.1134/S1070428024100038","url":null,"abstract":"<p>Tripotassium 2-(1-cyano-2,2-disulfidoethenyl)-1,1,3,3-tetracyanopropenide was synthesized for the first time by the reaction of carbon disulfide and malononitrile trimer. Its further transformations afforded 2-amino-4-(dicyanomethylidene)-4<i>H</i>-thiopyran-3,5-dicarbonitrile derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1897 - 1900"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024100038.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859758","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}
引用次数: 0
Synthesis, Molecular Docking Study, and Effect on the Methylation of Tumor DNA of Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidines Functionalized by Aromatic Groups and Azines 芳香族和氮基功能化苯并[4 ',5 ']咪唑[2 ',1 ':6,1]吡啶[2,3-d]嘧啶的合成、分子对接研究及对肿瘤DNA甲基化的影响
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100051
A. A. Harutyunyan, S. G. Israelyan, M. S. Safaryan, A. S. Sumbatyan, L. E. Nersesyan, A. S. Aharonyan, I. S. Danielyan, R. E. Muradyan, A. S. Sargsyan, A. A. Hambardzumyan, H. A. Panosyan
{"title":"Synthesis, Molecular Docking Study, and Effect on the Methylation of Tumor DNA of Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidines Functionalized by Aromatic Groups and Azines","authors":"A. A. Harutyunyan,&nbsp;S. G. Israelyan,&nbsp;M. S. Safaryan,&nbsp;A. S. Sumbatyan,&nbsp;L. E. Nersesyan,&nbsp;A. S. Aharonyan,&nbsp;I. S. Danielyan,&nbsp;R. E. Muradyan,&nbsp;A. S. Sargsyan,&nbsp;A. A. Hambardzumyan,&nbsp;H. A. Panosyan","doi":"10.1134/S1070428024100051","DOIUrl":"10.1134/S1070428024100051","url":null,"abstract":"<p>6-Benzyl-4-styrylbenzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-<i>d</i>]pyrimidines and their conjugates with uracil, 5-fluorouracil, and 6-azauracile were synthesized. In addition to the previous findings, it was found that the reaction of 4-methyl-2-phenyl-5,6-dihydrobenzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-<i>d</i>]pyrimidine with aromatic aldehydes in acetic anhydride, depending on the nucleophilicity of the aldehyde carbonyl group, involved both C<sup>6</sup>H<sub>2</sub> methylene group at the α-position with respect to the benzimidazole fragment and the 4-methyl group. The results of molecular docking study of the synthesized compounds and their effect on the methylation of tumor DNA are presented.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1909 - 1920"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859759","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, Antimicrobial Activity, and Molecular Docking Studies of Triazole-Tethered Piperazine Pharmacophores 三唑系哌嗪类药物的合成、抗菌活性和分子对接研究
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100129
C. R. Savajjera, L. A. Shastri, S. K. Praveen Kumar, N. P. Dalbanjan, S. D. Joshi
{"title":"Synthesis, Antimicrobial Activity, and Molecular Docking Studies of Triazole-Tethered Piperazine Pharmacophores","authors":"C. R. Savajjera,&nbsp;L. A. Shastri,&nbsp;S. K. Praveen Kumar,&nbsp;N. P. Dalbanjan,&nbsp;S. D. Joshi","doi":"10.1134/S1070428024100129","DOIUrl":"10.1134/S1070428024100129","url":null,"abstract":"<p>A series of piperazine-containing 1,2,3-triazoles were synthesized by employing the regioselective click chemistry approach using copper(I) catalyst. The synthesized compounds were evaluated for their antibacterial activity against Gram-negative (<i>P. aeruginosa</i>, <i>E. coli</i>) and Gram-positive bacteria (<i>B. subtilis</i>, <i>S. aureus</i>) and fungicidal activity against <i>C. albicans</i> and <i>A. niger</i> by resazurin-based micro-broth dilution method. Compounds <b>6a</b>, <b>6e</b>, <b>6f</b>, and <b>6g</b> exhibited significant activity compared to the standard drug ampicillin, while compounds <b>6f</b> and <b>6g</b> showed higher activity compared to standard drug fluconazole. Furthermore, the docking studies were performed to provide an insight into the binding mode of the most active compounds with the target proteins.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1968 - 1979"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859690","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 3-(Organyloxymethyl)tetrahydro-1,3-oxazines 3-（有机氧甲基）四氢-1,3-恶嗪的合成
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100087
V. M. Farzaliyev, M. T. Abbasova, X. K. Efendiyeva, Z. K. Soltanova, L. M. Shahgeldiyeva, L. R. Safarova, N. A. Alieva
{"title":"Synthesis of 3-(Organyloxymethyl)tetrahydro-1,3-oxazines","authors":"V. M. Farzaliyev,&nbsp;M. T. Abbasova,&nbsp;X. K. Efendiyeva,&nbsp;Z. K. Soltanova,&nbsp;L. M. Shahgeldiyeva,&nbsp;L. R. Safarova,&nbsp;N. A. Alieva","doi":"10.1134/S1070428024100087","DOIUrl":"10.1134/S1070428024100087","url":null,"abstract":"<p>3-(Organyloxymethyl)tetrahydro-1,3-oxazines were synthesized by the condensation–heterocycliza­tion of 3-aminopropan-1-ol, formaldehyde, and various hydroxyl-containing compounds. 3,3′-methylenebis­(tetra­hydro-2<i>H</i>-1,3-oxazine) was also formed as byproduct in ~10% yield. The yield of the title compounds increased in parallel with the length of the hydrocarbon chain in the initial alcohol. Furthermore, the yields of the target products obtained from unbranched alcohols were higher than in the reactions with their branched isomers. The product structure was determined by <sup>13</sup>C NMR spectroscopy. The effect of the organyloxymethyl substituent on the <sup>13</sup>C chemical shifts of the endocyclic carbons in comparison to unsubstituted tetrahydro-1,3-oxazine and 3-methyltetrahydro-1,3-oxazine was studied.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1945 - 1949"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858725","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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