A. V. Velikorodov, E. N. Kutlalieva, N. V. Zolotareva, N. N. Stepkina, S. B. Nosachev
{"title":"Synthesis of Methyl (Hetarylalkyl) N-Allyl-N-phenylcarbamates and Their Transformation into 4,5-Dihydroisoxazole Derivatives","authors":"A. V. Velikorodov, E. N. Kutlalieva, N. V. Zolotareva, N. N. Stepkina, S. B. Nosachev","doi":"10.1134/S1070428024070078","DOIUrl":"10.1134/S1070428024070078","url":null,"abstract":"<p>Alkylation of aromatic carbamates with allyl bromide under liquid-liquid phase transfer catalysis furnished the corresponding <i>N</i>-allyl derivatives of aryl carbamates in 63–71% yields. It was found that the cycloaddition of arene carbonitrile <i>N</i>-oxides, generated <i>in situ</i> from the corresponding oximes in the presence of chloramine T, to the allyl fragment upon boiling in ethanol led to the production of the corresponding 4,5-dihydroisoxazole derivatives in 89–96% yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1186 - 1192"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434794","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}
A. D. Yudina, T. V. Boykova, O. Yu. Ganz, L. A. Klimaeva, A. A. Burmistrova, T. O. Karpunina, E. V. Okina
{"title":"1-Hydro- and 1,10-Dihydro-1,10-phenanthrolinium Perchlorates in Electrocatalytic Production of Molecular Hydrogen","authors":"A. D. Yudina, T. V. Boykova, O. Yu. Ganz, L. A. Klimaeva, A. A. Burmistrova, T. O. Karpunina, E. V. Okina","doi":"10.1134/S1070428024070133","DOIUrl":"10.1134/S1070428024070133","url":null,"abstract":"<p>The electrochemical and electrocatalytic properties of 1-hydro-1,10-phenanthrolinium and 1,10-dihydro-1,10-phenanthrolinium perchlorates in formation of molecular hydrogen in the presence of CF<sub>3</sub>COOH were studied by cyclic voltammetry. The presence of hydrogen atoms at nitrogen atoms in the heterocyclic compounds strongly influences the electrochemical properties of the compounds and the efficiency of the electrocatalytic process. In going from 1-hydro-1,10-phenanthrolinium perchlorate to 1,10-dihydro-1,10-phenanthrolinium perchlorate, the process efficiency increases (TOF and TON values are higher), despite identical mechanisms. The reaction mechanisms were studied by DFT, and the key intermediates were revealed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1233 - 1238"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434901","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}
K. Pushpa Kumar, M. Varalakshmi, Y. B. Kiran, U. Nagarjuna, M. Rajaswi Devi, D. Venkataramana Reddy, C. Naga Raju
{"title":"Synthesis and Bioassay of New Urea and Thiourea Derivatives of 4-Aminobenzohydrazide","authors":"K. Pushpa Kumar, M. Varalakshmi, Y. B. Kiran, U. Nagarjuna, M. Rajaswi Devi, D. Venkataramana Reddy, C. Naga Raju","doi":"10.1134/S1070428024070108","DOIUrl":"10.1134/S1070428024070108","url":null,"abstract":"<p>A series of new urea <b>3a–3d</b> and thiourea derivatives <b>5a–5f</b> have been synthesized in high yields (77–88%) by the reaction of substituted aryl isocyanates <b>2a–2d</b> and substituted aryl isothiocynates <b>4a–4f</b> with 4-aminobenzoic hydrazide <b>1.</b> The structures of all the synthesized compounds were characterized by IR, NMR (<sup>1</sup>H and <sup>13</sup>C), mass and elemental analyses. The synthesized compounds were screened for their anti-microbial activity. The present study revealed that Gram-negative and positive bacteria such as <i>Escherichia coli</i> and <i>Streptococcus aureus</i> were more susceptible to the solvent extracts. The methanol and acetone extracts of the newly synthesized compounds were evaluated for <i>in vitro</i> antibacterial activity against human pathogenic bacteria <i>Escherichia coli</i> and <i>Streptococcus aureus</i> and antifungal activity against <i>Aspergillus niger</i> and <i>Aspergillus oryzae</i>. Compound <b>5e</b> have exhibited good antibacterial and antifungal activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1209 - 1216"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434878","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}
{"title":"Synthetic Pathway of [2,4-Dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic Acid","authors":"V. G. Dudarev, M. I. Vasendin, A. V. Moskvin","doi":"10.1134/S1070428024070029","DOIUrl":"10.1134/S1070428024070029","url":null,"abstract":"<p>Synthetic route of 3,5-dichlorosalicylic acid anilide containing the carboxymethoxy group in the aniline fragment in <i>ortho</i>-position to amide group has been suggested. The obtained intermediate (2,4-dichloro-6-nitrophenoxy)-<i>N</i>,<i>N</i>-dimethylacetamide has been reduced into the amine and acylated with 3,5-dichloro-2-hydroxybenzoyl chloride, and then protective <i>N,N</i>-dimethylamide group has been selectively hydrolyzed in an alkaline medium. Without protection of the carboxyl group, the reaction with 3,5-dichloro-2-hydroxybenzoyl chloride has afforded mainly 6,8-dichloro-2<i>H</i>-1,4-benzoxazin-3(4<i>H</i>)-one.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1157 - 1163"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434773","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}
K. A. Alheety, N. M. Jamel, W. M. Abd-Al Hameed, M. S. Al-Rawi, J. H. Tomma
{"title":"Synthesis and Study of the Biological Activity of New Compounds Derived from 4-(5-Phenyl-1,3,4-oxadiazole-2-yl)aniline","authors":"K. A. Alheety, N. M. Jamel, W. M. Abd-Al Hameed, M. S. Al-Rawi, J. H. Tomma","doi":"10.1134/S1070428024070261","DOIUrl":"10.1134/S1070428024070261","url":null,"abstract":"<p>A new series of <i>N</i>-acyl derivatives (<b>4a–4d</b>) and Azetidin-2-one derivatives (<b>5a</b>, <b>5b</b>) containing a 1,3,4-oxadiazole ring were prepared by sequence reactions. The new Schiff bases (<b>3a–3d</b>) used as starting materials were prepared via condensation of (4-(5-phenyl-1,3,4-oxadiazole-2yl)aniline) with four replaced aromatic dialdehyde (<b>2a–2d</b>). The newly synthesized Schiff bases (<b>3a–3d</b>) reacted with, acetyl chloride in the dry benzene to get new derivatives (<b>4a–4d</b>). While the second path was towards the formation of new Azetidin-2-one derivatives (<b>5a</b>, <b>5b</b>) from cyclization reaction of the Schiff bases with chloroacetylchloride in dioxan and triethylamine at 0–5°C. Synthesized compounds had been characterized by FT-IR and <sup>1</sup>H NMR spectra in order to elucidate their structures. Finally, the resulting products were evaluated for it is efficacy measurements against two types of bacteria showed excellent to good efficacy antibacterial activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1342 - 1347"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434779","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}
{"title":"Synthesis and Antioxidant Activity of New Bis-1,3,4-oxadiazoles, Bis-1,3,4-thiadiazoles, and Their Derivatives","authors":"S. V. Dilanyan, Zh. M. Buniatyan, H. A. Panosyan","doi":"10.1134/S1070428024070224","DOIUrl":"10.1134/S1070428024070224","url":null,"abstract":"<p>Bis-1,3,4-oxadiazoles and bis-1,3,4-thiadiazoles with aryl and alkyl linkers have been synthesized. The pharmacophore electron-deficient groups (carboxylic, nitrile) have been introduced into the molecule to increase their hydrophilicity and potential biological activity. Functionalized compounds have demonstrated a new type of biological activity, i.e., inhibition of lipid oxidation revealed as a decrease in the amount of MDA.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1301 - 1306"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434785","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}
G. V. Remezova, G. F. Sakhautdinova, I. M. Sakhautdinov
{"title":"Synthesis of Analog of Bistetrahydroisoquinoline Alkaloids Based on N-Homoveratrylmaleimide","authors":"G. V. Remezova, G. F. Sakhautdinova, I. M. Sakhautdinov","doi":"10.1134/S1070428024070285","DOIUrl":"10.1134/S1070428024070285","url":null,"abstract":"<p>A new method for the synthesis of a bisbenzylisoquinoline base with a diphenyl oxide fragment based on phosphorane obtained from <i>N</i>-homoveratrylmaleimide has been suggested.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1351 - 1354"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434750","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}
N. M. Binhydra, A. P. Sarkate, M. S. Wagh, S. S. Pawar, P. K. Kankal, G. V. Patwekar, A. A. Pund, D. N. Pansare, R. N. Shelke, S. V. Bhandari
{"title":"One-Pot Synthesis of the 5-Benzylidene-2-thioxothiazolidin-4-one Derivative and Screening of Metal Catalysts Using Fruit Juice","authors":"N. M. Binhydra, A. P. Sarkate, M. S. Wagh, S. S. Pawar, P. K. Kankal, G. V. Patwekar, A. A. Pund, D. N. Pansare, R. N. Shelke, S. V. Bhandari","doi":"10.1134/S1070428024070121","DOIUrl":"10.1134/S1070428024070121","url":null,"abstract":"<p>Here in this article we described the synthesis of 5-benzylidene-2-thioxothiazolidin-4-one derivative via one pot reaction mechanism with excellent yield in short reaction time using conventional and microwave irradiation methods. Lemon juice used as a green solvent, ammonium ferrous sulfate as catalyst in the presence of sodium citrate buffer as base reduces the time cycle and increased the yields. In addition, screening of various metal catalysts was studied. This methodology gave excellent yield and purity as compared with earlier reported process. The advantages of this process are cost-effective, short reaction time, high atom economy and environmental friendly. In addition, as compared to traditional heating approach, the microwave-assisted synthesis offered outstanding yields.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1225 - 1232"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434880","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}
A. Y. Ershov, A. A. Martynenkov, I. V. Lagoda, A. A. Batyrenko
{"title":"Application of the ANRORC Process for Directional Synthesis of 5-Ureido-2-pyrazolines as Biologically Active Co-Ligand of Gold Glyco-Nanoparticles","authors":"A. Y. Ershov, A. A. Martynenkov, I. V. Lagoda, A. A. Batyrenko","doi":"10.1134/S1070428024070194","DOIUrl":"10.1134/S1070428024070194","url":null,"abstract":"<p>Interaction of 1-phenyl-4,6-dimethylpyrimidine-2(1<i>H</i>)-one with 4-mercaptobuturic acid hydrazide proceeds as ANRORC (Addition of the Nucleophile–Ring Opening–Ring Closure) process and results in the formation with 60% yield of 1-(4-mercaptobutanoyl)-3,5-dimethyl-5-(3-phenylcarbamoylamino)-2-pyrazoline as promising сo-ligand for the preparation of gold glyco-nanoparticles for biomedical purposes.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1274 - 1276"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434904","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}
Xiu-Jun Wang, Hui-Jie Chen, Zhi-Yu Liu, Yue Qiao, Xue-Bao Wang, Bin-Yan Wang, Wen-Tao Jiang, Xiao Hou, Meng-Meng Wang, Kuang-Qi Li, Si-Yi Zhang, Han-Xue Li, Bin Liu, Jing Ji, Ming-Li Yang
{"title":"Design, Synthesis, and Antiproliferative Evaluation of Piperine Derivatives","authors":"Xiu-Jun Wang, Hui-Jie Chen, Zhi-Yu Liu, Yue Qiao, Xue-Bao Wang, Bin-Yan Wang, Wen-Tao Jiang, Xiao Hou, Meng-Meng Wang, Kuang-Qi Li, Si-Yi Zhang, Han-Xue Li, Bin Liu, Jing Ji, Ming-Li Yang","doi":"10.1134/S1070428024070212","DOIUrl":"10.1134/S1070428024070212","url":null,"abstract":"<p>–The parent nuclear structure of piperine served as the basis for the design and synthesis of thirteen derivatives through nucleophilic substitution method. These derivatives were subsequently characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HR-MS analysis. The antiproliferative activities of these compounds against 293T human normal cells, as well as MDA-MB-231 (breast) and Hela (cervical) cancer cell lines were assessed through the MTT assay. Compound <b>4b</b> exhibited remarkable antiproliferative activity against Hela cells (IC<sub>50</sub> = 1.80 μM), surpassing that of both 5-fluorouracil (IC<sub>50</sub> = 44.58 μM) and piperine itself. Furthermore, subsequent investigations revealed that compound <b>4b</b> displayed significant anti-proliferation, anti-migration and anti-invasion effects on Hela cells. These findings suggest that compound <b>4b</b> may be a promising lead compound for the treatment of cervical carcinoma.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1288 - 1300"},"PeriodicalIF":0.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434777","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}