Pub Date : 2024-05-19DOI: 10.1134/s1070428024030023
D. I. Antonov, M. V. Dmitriev, I. A. Kuchumov, A. N. Maslivets
Abstract
5-Aryl-1H-pyrrole-2,3-diones reacted with amidoximes to give enamines containing a 1,2,4-oxadiazole fragment that are potential precursors to novel 1H-pyrrole-2,3-diones. The described reaction is the first example of recyclization of 4-unsubstitued 5-aryl-1H-pyrrole-2,3-diones by the action of 1,4-binucleophiles.
{"title":"Recyclization of 5-Aryl-1H-pyrrole-2,3-diones with Amidoximes. Synthesis of Enamines Containing a 1,2,4-Oxadiazole Fragment","authors":"D. I. Antonov, M. V. Dmitriev, I. A. Kuchumov, A. N. Maslivets","doi":"10.1134/s1070428024030023","DOIUrl":"https://doi.org/10.1134/s1070428024030023","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>5-Aryl-1<i>H</i>-pyrrole-2,3-diones reacted with amidoximes to give enamines containing a 1,2,4-oxadiazole fragment that are potential precursors to novel 1<i>H</i>-pyrrole-2,3-diones. The described reaction is the first example of recyclization of 4-unsubstitued 5-aryl-1<i>H</i>-pyrrole-2,3-diones by the action of 1,4-binucleophiles.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153395","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030151
O. Marvi, S. Arshadi
Abstract
An environmentally friendly and highly efficient method for onion extract-catalyzed microwave-assisted solvent- free synthesis of pyrroles via Paal–Knorr reaction with hexane-2,5-dione has been developed. This method is applicable to a wide range of aromatic, aliphatic, and heterocyclic primary amines, and it affords various pyrrole derivatives in good to excellent yields (up to 98%) at 80°C. The use of onion extract as catalyst makes the process environmentally benign.
{"title":"Onion (Allium cepa L.) Extract: A Green and Eco-friendly Catalyst for MW-Assisted Solvent-Free Synthesis of Pyrroles via Paal–Knorr Reaction","authors":"O. Marvi, S. Arshadi","doi":"10.1134/s1070428024030151","DOIUrl":"https://doi.org/10.1134/s1070428024030151","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>An environmentally friendly and highly efficient method for onion extract-catalyzed microwave-assisted solvent- free synthesis of pyrroles via Paal–Knorr reaction with hexane-2,5-dione has been developed. This method is applicable to a wide range of aromatic, aliphatic, and heterocyclic primary amines, and it affords various pyrrole derivatives in good to excellent yields (up to 98%) at 80°C. The use of onion extract as catalyst makes the process environmentally benign.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153323","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030199
V. B. Das, B. Poojary, V. Kamat, S. Hamzad, P. Suman
Abstract
A library of 1,2,3-triazole-containing hydrazones have been synthesized via Cu(I)-mediated 1,3-dipolar cycloaddition reaction. The structures of the synthesized compounds were elucidated by NMR, mass spectrometry, and IR spectroscopy. The synthesized compounds were screened for their cytotoxicity by MTT assay against MCF-7 cancer cell line, and a number of derivatives showed good anticancer potential. In silico molecular docking study revealed good binding affinity of the synthesized compounds for the target HER2 kinase domain complexed with TAK-285 (PDB ID: 3RCD).
{"title":"Synthesis, Anticancer Evaluation, and Molecular Docking Study of 1,2,3-Triazole-Containing Hydrazones as Potential HER2 Kinase Inhibitors","authors":"V. B. Das, B. Poojary, V. Kamat, S. Hamzad, P. Suman","doi":"10.1134/s1070428024030199","DOIUrl":"https://doi.org/10.1134/s1070428024030199","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A library of 1,2,3-triazole-containing hydrazones have been synthesized via Cu(I)-mediated 1,3-dipolar cycloaddition reaction. The structures of the synthesized compounds were elucidated by NMR, mass spectrometry, and IR spectroscopy. The synthesized compounds were screened for their cytotoxicity by MTT assay against MCF-7 cancer cell line, and a number of derivatives showed good anticancer potential. In silico molecular docking study revealed good binding affinity of the synthesized compounds for the target HER2 kinase domain complexed with TAK-285 (PDB ID: 3RCD).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153468","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030114
Z. S. Kinzyabaeva, Z. N. Fazletdinova, D. Sh. Sabirov
Abstract
A method has been developed for the synthesis of new fused 1,4-benzoxazine monoadducts of fullerene C60 by the reaction with 2-aminophenols (2-aminophenol, 2-amino-4-methylphenol, 3-amino-[1,1′-biphenyl]-4-ol) in the presence of LiOH and Pb(OAc)4. A probable reaction mechanism has been proposed.
{"title":"Synthesis of 1,4-Benzoxazine Adducts of Fullerene C60 in the Presence of Lead(IV) Acetate","authors":"Z. S. Kinzyabaeva, Z. N. Fazletdinova, D. Sh. Sabirov","doi":"10.1134/s1070428024030114","DOIUrl":"https://doi.org/10.1134/s1070428024030114","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A method has been developed for the synthesis of new fused 1,4-benzoxazine monoadducts of fullerene C<sub>60</sub> by the reaction with 2-aminophenols (2-aminophenol, 2-amino-4-methylphenol, 3-amino-[1,1′-biphenyl]-4-ol) in the presence of LiOH and Pb(OAc)<sub>4</sub>. A probable reaction mechanism has been proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153366","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030102
E. Kh. Makarova, A. A. Makarov, U. M. Dzhemilev, V. A. D’yakonov
Abstract
New amides of (5Z,9Z)-eicosa-5,9-dienoic acid, which is a highly active topoisomerase I/II inhibitor, were synthesized via Cp2TiCl2-catalyzed intermolecular cross-cyclomagnesiation of aliphatic and oxygen-containing 1,2-dienes as the key step.
{"title":"Synthesis of Amides Based on Biologically Active (5Z,9Z)-Eicosa-5,9-dienoic Acid","authors":"E. Kh. Makarova, A. A. Makarov, U. M. Dzhemilev, V. A. D’yakonov","doi":"10.1134/s1070428024030102","DOIUrl":"https://doi.org/10.1134/s1070428024030102","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>New amides of (5Z,9Z)-eicosa-5,9-dienoic acid, which is a highly active topoisomerase I/II inhibitor, were synthesized via Cp<sub>2</sub>TiCl<sub>2</sub>-catalyzed intermolecular cross-cyclomagnesiation of aliphatic and oxygen-containing 1,2-dienes as the key step.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153321","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030175
N. Uludag
Abstract
A series of substituted ethyl 5-phenyl-1,2-oxazole-3-carboxylates were synthesized in good to excellent yields in one step using hydroxylamine base and ethyl 2,4-dioxo-4-(4-R-phenyl)butanoates bearing both electron-donating and electron-withdrawing moieties on the benzene ring, and antioxidant properties of the products were investigated by the DPPH method. The proposed method is suitable for the large-scale production of isoxazole derivatives.
{"title":"New Synthesis of Some Isoxazole Derivatives and Their Antioxidant Properties","authors":"N. Uludag","doi":"10.1134/s1070428024030175","DOIUrl":"https://doi.org/10.1134/s1070428024030175","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A series of substituted ethyl 5-phenyl-1,2-oxazole-3-carboxylates were synthesized in good to excellent yields in one step using hydroxylamine base and ethyl 2,4-dioxo-4-(4-R-phenyl)butanoates bearing both electron-donating and electron-withdrawing moieties on the benzene ring, and antioxidant properties of the products were investigated by the DPPH method. The proposed method is suitable for the large-scale production of isoxazole derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153316","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030047
S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan
Abstract
Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-d]pyrimidin-4(1H)-ones by the action of hydrazine hydrate. The condensation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-aminothienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.
{"title":"Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate","authors":"S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan","doi":"10.1134/s1070428024030047","DOIUrl":"https://doi.org/10.1134/s1070428024030047","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-<i>d</i>]pyrimidin-4(1<i>H</i>)-ones by the action of hydrazine hydrate. The condensation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-aminothienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153687","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030205
F. Yilmaz
Abstract
A series of 1,2,4-triazol-3-one derivatives were synthesized by using conventional heating and microwave irradiation techniques. Microwave syntheses of the target compounds were carried out by using both a domestic microwave oven and a monomode microwave reactor. The results showed that the use of microwave technique is advantageous in terms of time, low solvent loading, yield, and efficiency. The synthesized compounds were tested for their antioxidant and antiurease activities. The antioxidant activity was evaluated by using ABTS [2,2′-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt] radical scavenging and cupric ion reducing antioxidant capacity (CUPRAC) methods. Most of the compounds showed good antioxidant activity, especially compound 8d showed an SC50 value of 71.062±9.31 μM in comparison to Trolox used as standard (SC50 = 210.04±16.22 μM). According to the urease inhibitory activity results, most of the compounds showed better activity than thiourea (IC50 = 0.5027±0.0293 μM); in particular, compound 8a exhibited an IC50 value of 0.3070±0.0394 μM.
{"title":"Green Synthesis and Biological Evaluation of Some 1,2,4-Triazol-3-ones","authors":"F. Yilmaz","doi":"10.1134/s1070428024030205","DOIUrl":"https://doi.org/10.1134/s1070428024030205","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A series of 1,2,4-triazol-3-one derivatives were synthesized by using conventional heating and microwave irradiation techniques. Microwave syntheses of the target compounds were carried out by using both a domestic microwave oven and a monomode microwave reactor. The results showed that the use of microwave technique is advantageous in terms of time, low solvent loading, yield, and efficiency. The synthesized compounds were tested for their antioxidant and antiurease activities. The antioxidant activity was evaluated by using ABTS [2,2′-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt] radical scavenging and cupric ion reducing antioxidant capacity (CUPRAC) methods. Most of the compounds showed good antioxidant activity, especially compound <b>8d</b> showed an SC<sub>50</sub> value of 71.062±9.31 μM in comparison to Trolox used as standard (SC<sub>50</sub> = 210.04±16.22 μM). According to the urease inhibitory activity results, most of the compounds showed better activity than thiourea (IC<sub>50</sub> = 0.5027±0.0293 μM); in particular, compound <b>8a</b> exhibited an IC<sub>50</sub> value of 0.3070±0.0394 μM.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153322","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}
Pub Date : 2024-05-19DOI: 10.1134/s107042802403014x
Shan Gao, Ai-Ling Wang, Ming-Zhe Wang
Abstract
A novel coumarin-derived Schiff base fluorescent probe was reported to detect Cu2+ ions in human cells. It was synthesized by the reaction between 7-(diethylamino)coumarin-3-carbohydrazide and pyridoxal 5′-phosphate. The probe has good stability and it exhibited obviously decreasing fluorescent response at λ 490 nm upon addition of Cu(II) ions. The fluorescent probe showed high selectivity for Cu(II) ions compared to other metal ions. The probe has been successfully applied to detect Cu(II) ions in human cells.
{"title":"A Coumarin-Based Fluorescent Probe for Selective Detection of Cu(II) and Imaging in Human Cell","authors":"Shan Gao, Ai-Ling Wang, Ming-Zhe Wang","doi":"10.1134/s107042802403014x","DOIUrl":"https://doi.org/10.1134/s107042802403014x","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A novel coumarin-derived Schiff base fluorescent probe was reported to detect Cu<sup>2+</sup> ions in human cells. It was synthesized by the reaction between 7-(diethylamino)coumarin-3-carbohydrazide and pyridoxal 5′-phosphate. The probe has good stability and it exhibited obviously decreasing fluorescent response at λ 490 nm upon addition of Cu(II) ions. The fluorescent probe showed high selectivity for Cu(II) ions compared to other metal ions. The probe has been successfully applied to detect Cu(II) ions in human cells.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153368","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}
Pub Date : 2024-05-19DOI: 10.1134/s1070428024030230
A. U. Isakhanyan, N. Z. Hakobyan, R. E. Muradyan, H. E. Tumajyan, H. A. Panosyan, A. A. Harutyunyan
Abstract
Schiff bases of the tetrahydropyran series have been synthesized by the condensation of 2-(tetrahydropyran-4-yl)ethanamines and tetrahydropyran-4-amine with 4-chloro, 4-fluoro-, and 4-(dimethylamino)benzaldehydes and thiophene-2-carbaldehyde. The synthesized compounds showed lower anti-inflammatory, analgesic, and antipyretic activities than those of diclofenac and indomethacin used as reference drugs.
{"title":"Synthesis and Anti-inflammatory, Analgesic, and Antipyretic Activities of Azomethine Derivatives of the Tetrahydropyran Series","authors":"A. U. Isakhanyan, N. Z. Hakobyan, R. E. Muradyan, H. E. Tumajyan, H. A. Panosyan, A. A. Harutyunyan","doi":"10.1134/s1070428024030230","DOIUrl":"https://doi.org/10.1134/s1070428024030230","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Schiff bases of the tetrahydropyran series have been synthesized by the condensation of 2-(tetrahydropyran-4-yl)ethanamines and tetrahydropyran-4-amine with 4-chloro, 4-fluoro-, and 4-(dimethylamino)benzaldehydes and thiophene-2-carbaldehyde. The synthesized compounds showed lower anti-inflammatory, analgesic, and antipyretic activities than those of diclofenac and indomethacin used as reference drugs.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153367","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}