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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
An Efficient Synthesis of Aromatic Aldehydes by Iron-Catalyzed Reductive Carbonylation of Aryl Iodides
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100233
R. Akkineni, K. Sheelam, S. P. Douglas, V. R. Battula
{"title":"An Efficient Synthesis of Aromatic Aldehydes by Iron-Catalyzed Reductive Carbonylation of Aryl Iodides","authors":"R. Akkineni,&nbsp;K. Sheelam,&nbsp;S. P. Douglas,&nbsp;V. R. Battula","doi":"10.1134/S1070428024100233","DOIUrl":"10.1134/S1070428024100233","url":null,"abstract":"<p>Reductive carbonylation of aryl halides (Hlg = Cl, Br, I) by using carbon monoxide as carbonyl source in the presence of iron catalyst, silyl hydride, and base under mild reaction conditions afforded the corresponding aromatic aldehydes. In this methodology, aryl iodides were conveniently transformed to aldehydes in moderate to excellent yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2044 - 2047"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859593","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
[TMBSPD][OMs]2: An Efficient Recyclable Ionic Liquid for the Synthesis of Bis(indolyl)methanes from Aldehydes or Ketones and Indoles at Ambient Temperature [TMBSPD][OMs]2：一种在常温下从醛或酮和吲哚合成双(吲哚基)甲烷的高效可回收离子液体
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100142
M. Janmohammadi, F. K. Behbahani
{"title":"[TMBSPD][OMs]2: An Efficient Recyclable Ionic Liquid for the Synthesis of Bis(indolyl)methanes from Aldehydes or Ketones and Indoles at Ambient Temperature","authors":"M. Janmohammadi,&nbsp;F. K. Behbahani","doi":"10.1134/S1070428024100142","DOIUrl":"10.1134/S1070428024100142","url":null,"abstract":"<p>An efficient synthesis of bis(indolyl)methanes by the reaction of aldehydes and ketones with indoles catalyzed by <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-tetramethyl-<i>N</i>,<i>N</i>′-bis(sulfo)biphenyl-4,4′-diaminium bis(methanesulfonate) ([TMBSPD][OMs]<sub>2</sub>) has been developed. The reaction proceeds in ethanol at room temperature to provide the desired products in good to excellent yields. The proposed methodology is characterized by a broad substrate scope, environmental friendliness, and cost efficiency.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1984 - 1990"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859692","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 Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogues Containing Polycyclic Fragments: XXI. N-(Adamantane-1-carbonyl]-N′-(haloaryl)selenoureas
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S107042802410004X
Ya. P. Kuznetsov, D. A. Pitushkin, G. M. Butov
{"title":"Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogues Containing Polycyclic Fragments: XXI. N-(Adamantane-1-carbonyl]-N′-(haloaryl)selenoureas","authors":"Ya. P. Kuznetsov,&nbsp;D. A. Pitushkin,&nbsp;G. M. Butov","doi":"10.1134/S107042802410004X","DOIUrl":"10.1134/S107042802410004X","url":null,"abstract":"<p>Selenoureas containing a halophenyl fragment were synthesized in 37–59% yields from adaman­tane-1-carbonyl isoselenocyanate and haloanilines. Replacement of the sulfur atom by selenium resulted in a reduction of the melting points of selenoureas by 8–47°C in comparison to their sulfur analogues. In silico screening showed that the most probable types of biological activity of the synthesized selenoureas are inhibition of human soluble epoxide hydrolase and anxiolytic activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1901 - 1908"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S107042802410004X.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858649","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
Pd(PPh3)4-Catalyzed Elimination of Acetic Acid from (±)-9α,11α,15α-Triacetoxycloprostenol 4-Methoxybenzyl Ester
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100026
V. V. Zagitov, N. S. Vostrikov, M. S. Miftakhov
{"title":"Pd(PPh3)4-Catalyzed Elimination of Acetic Acid from (±)-9α,11α,15α-Triacetoxycloprostenol 4-Methoxybenzyl Ester","authors":"V. V. Zagitov,&nbsp;N. S. Vostrikov,&nbsp;M. S. Miftakhov","doi":"10.1134/S1070428024100026","DOIUrl":"10.1134/S1070428024100026","url":null,"abstract":"<p>Attempted replacement of the allylic C<sup>15</sup>-acetate group in 9α,11α,15α-triacetoxycloprostenol 4-methoxybenzyl ester by tosyl group under phase-transfer conditions [CH<sub>2</sub>Cl<sub>2</sub>/H<sub>2</sub>O, R<sub>3</sub>R′N<sup>+</sup>Hlg<sup>–</sup>, NaOH, TsOH, Pd(PPh<sub>3</sub>)<sub>4</sub>] led to the formation of the corresponding (13<i>E</i>,15<i>Z</i>) derivative in a moderate yield as a result of elimination of acetic acid. The same product was obtained with high yield and stereoselectivity when the reaction was carried out in THF in the presence of Pd(PPh<sub>3</sub>)<sub>4</sub> and NaH.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1892 - 1896"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024100026.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858728","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 of Polyfunctionalized [1,2′-Bipyridin]-1-ium Chlorides 多官能化[1,2′-联吡啶]-1-鎓氯化物的合成
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100221
P. I. Tuktin, A. I. Ershova, S. V. Karpov, V. V. Andreeva, O. V. Ershov
{"title":"Synthesis of Polyfunctionalized [1,2′-Bipyridin]-1-ium Chlorides","authors":"P. I. Tuktin,&nbsp;A. I. Ershova,&nbsp;S. V. Karpov,&nbsp;V. V. Andreeva,&nbsp;O. V. Ershov","doi":"10.1134/S1070428024100221","DOIUrl":"10.1134/S1070428024100221","url":null,"abstract":"<p>A procedure has been developed for the synthesis of polyfunctionalized pyridine derivatives, 6′-amino-4′-aryl-3′,5′-dicyano[1,2′-bipyridin]-1-ium chlorides from simple precursors, malononitrile and aromatic aldehydes.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2040 - 2043"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859591","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 Dipolar Chromophores Based on Polyfluorinated Triphenyl-4,5-dihydro-1H-pyrazoles and Dicyanoisophorone with a Thiophene Fragment in the Polymethine Chain 基于多氟化三苯基-4,5-二氢-1H-吡唑和二氰基异佛尔酮的双极性发色团与聚甲基链中的噻吩片段的合成
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100063
V. V. Shelkovnikov, A. V. Ishchenko, I. Yu. Kargapolova, N. A. Orlova
{"title":"Synthesis of Dipolar Chromophores Based on Polyfluorinated Triphenyl-4,5-dihydro-1H-pyrazoles and Dicyanoisophorone with a Thiophene Fragment in the Polymethine Chain","authors":"V. V. Shelkovnikov,&nbsp;A. V. Ishchenko,&nbsp;I. Yu. Kargapolova,&nbsp;N. A. Orlova","doi":"10.1134/S1070428024100063","DOIUrl":"10.1134/S1070428024100063","url":null,"abstract":"<p>A series of donor–acceptor polymethine dyes containing a polyfluorinated triphenyl-4,5-dihydro-1<i>H</i>-pyrazole fragment as donor moiety, dicyanoisophorone fragment as acceptor moiety, and polymethine chain including a thiophene fragment have been synthesized as potential nonlinear optical chromophores. The electronic absorption spectra of the synthesized dyes showed a long-wavelength maximum at λ 540–550 nm, which is shifted by 40 nm to the red region compared to their analogues without a thiophene bridge. The dyes displayed luminescence in chloroform solution with an emission maximum at λ 740–760 nm and a Stokes shift of 200–210 nm (5000 cm<sup>–1</sup>).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1921 - 1931"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024100063.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859760","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
Adamantane: On the 90th Anniversary of Its Appearance in Chemical Science 金刚烷纪念金刚烷出现在化学科学领域 90 周年
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100014
E. A. Shokova, J. K. Kim, V. V. Kovalev
{"title":"Adamantane: On the 90th Anniversary of Its Appearance in Chemical Science","authors":"E. A. Shokova,&nbsp;J. K. Kim,&nbsp;V. V. Kovalev","doi":"10.1134/S1070428024100014","DOIUrl":"10.1134/S1070428024100014","url":null,"abstract":"<p>The review describes the history of the development of adamantane chemistry and shows moments that stimulated rise in the studies, as well as the main lines of research in this field and prospects thereof, on the basis of published data (up to 2024) with an emphasis on the last two decades.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1831 - 1891"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858721","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, DFT Calculations, and Crystal Structures of Three Series of Five-Membered Heterocyclic Monoimine Compounds
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S1070428024100208
B. Su, Y. Tan, Sh. Wu, H. Sun, Q. Han, L. Ding
{"title":"Microwave-Assisted Synthesis, DFT Calculations, and Crystal Structures of Three Series of Five-Membered Heterocyclic Monoimine Compounds","authors":"B. Su,&nbsp;Y. Tan,&nbsp;Sh. Wu,&nbsp;H. Sun,&nbsp;Q. Han,&nbsp;L. Ding","doi":"10.1134/S1070428024100208","DOIUrl":"10.1134/S1070428024100208","url":null,"abstract":"<p>Three series of five-membered heterocyclic Schiff bases were synthesized by the condensation of 2-acetylpyrrole, 2-acetylthiophene, and 2-acetylfuran with substituted anilines under microwave irradiation. All compounds were fully characterized by <sup>1</sup>H NMR and IR spectra and elemental analyses, and the structures of six compounds were determined by X-ray single crystal diffraction. The reactions of 2-acetylpyrrole and 2-acetylthiophene with anilines gave 1:1 condensation products, whereas the condensations with 2-acetylfuran involved 2 equiv of substituted anilines and were accompanied by transformation of the furan ring to pyrrole via Paal–Knorr reaction. A probable reaction mechanism was proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2026 - 2035"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858650","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 New 1-(4-Anilinophenyl)-1H-pyrrole-2,5-diones
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1134/S107042802410021X
O. A. Kolyamshin, Yu. N. Mitrasov, V. A. Danilov, Yu. Yu. Pylchikova
{"title":"Synthesis of New 1-(4-Anilinophenyl)-1H-pyrrole-2,5-diones","authors":"O. A. Kolyamshin,&nbsp;Yu. N. Mitrasov,&nbsp;V. A. Danilov,&nbsp;Yu. Yu. Pylchikova","doi":"10.1134/S107042802410021X","DOIUrl":"10.1134/S107042802410021X","url":null,"abstract":"<p>The reaction of <i>N</i><sup>1</sup>-phenyl- and <i>N</i><sup>1</sup>-(4-methoxyphenyl)benzene-1,4-diamines with maleic anhydride gave the corresponding maleic acid monoamides whose cyclization in the presence of <i>p</i>-toluenesulfonic acid afforded 1-[4-anilino- and 4-(4-methoxyanilino)phenyl]-1<i>H</i>-pyrrole-2,5-diones.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"2036 - 2039"},"PeriodicalIF":0.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S107042802410021X.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858651","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
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