{"title":"Efficient and Green Synthesis of Novel 2-Amino-3-cyano-6-(phosphonoethyl)-4H-pyrans","authors":"I. Lamouchi, S. Touil","doi":"10.1134/S1070428025600147","DOIUrl":"10.1134/S1070428025600147","url":null,"abstract":"<p>Herein we report a convenient and green synthesis of a new class of phosphonopyrans—2-amino-3-cyano-6-phosphonoethyl-4<i>H</i>-pyrans—through the K<sub>2</sub>CO<sub>3</sub>-catalyzed reaction of malononitrile with γ-keto-δ-alkenylphosphine oxides. The reaction proceeds under operationally simple and mild conditions, employs a low-cost and an environmentally benign catalyst and ethanol as a green solvent.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1492 - 1498"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242798","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. A. Harutyunyan, A. S. Sumbatyan, S. G. Israelyan, A. A. Hambardzumyan, H. А. Panosyan
{"title":"Synthesis and Docking Study of 6-Substituted Indolo[2,3-b]quinoxalines","authors":"A. A. Harutyunyan, A. S. Sumbatyan, S. G. Israelyan, A. A. Hambardzumyan, H. А. Panosyan","doi":"10.1134/S1070428025601591","DOIUrl":"10.1134/S1070428025601591","url":null,"abstract":"<p>6-(2-Bromoethyl)-6<i>H</i>-indolo[2,3-<i>b</i>]quinoxaline was synthesized and reacted with arylamines to obtain <i>N</i>-(2-[6<i>H</i>-indolo[2,3-<i>b</i>]quinoxalin-6-yl)ethyl]arylamines and <i>N</i>,<i>N</i>-disubstituted 4-methylaniline. Previosly unknown 6-vinyl- and 6-(2-azidoethyl) derivatives of 6-(2-bromoethyl)-6<i>H</i>-indolo[2,3-<i>b</i>]quinoxaline and indolo[2,3-<i>b</i>]quinoxaline–pyrimidine and 1,2-bis(6<i>H</i>-indolo[2,3-<i>b</i>]quinoxalin-6-yl)ethane hybrids were also synthesized. Molecular docking studies of the synthesized indolo[2,3-b]quinoxaline derivatives against 4 different receptors indicated high predicted activity for the indoloquinoxaline–pyrimidine conjugate.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1465 - 1472"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242818","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}
M. P. Yakovleva, I. S. Nazarov, K. M. Saitov, G. Y. Ishmuratov, A. G. Tolstikov
{"title":"Efficient Synthesis of Optically Pure Macrocyclic Polylactones from Castor Oil and Sulfurous and Sebacic Acid Dichlorides","authors":"M. P. Yakovleva, I. S. Nazarov, K. M. Saitov, G. Y. Ishmuratov, A. G. Tolstikov","doi":"10.1134/S1070428025601682","DOIUrl":"10.1134/S1070428025601682","url":null,"abstract":"<p>An effective synthesis of optically pure macrocyclic polylactones is developed, involving the [1+1] condensation of a natural triol (castor oil) with thionyl chloride in carbon tetrachloride in the presence of DMF as a base and (<i>N</i>,<i>N</i>-dimethylamino)pyridine as a catalyst and followed by the [1+1] condensation of the resulting macrocyclic alcohol with sebacoyl chloride under similar conditions.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1422 - 1426"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242768","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}
Heta B. Vasveliya, Jignesh H. Pandya, Ghanshyam L. Jadav, Amita J. Jivani, Jyoti Kuchhadiya
{"title":"Design, Synthesis, and In Vitro α-Amylase Inhibitory Activity of 6-Bromo-1-[phenyl(quinolin-3-yl)amino]methyl)naphthalen-2-ol Betti Bases","authors":"Heta B. Vasveliya, Jignesh H. Pandya, Ghanshyam L. Jadav, Amita J. Jivani, Jyoti Kuchhadiya","doi":"10.1134/S1070428025600214","DOIUrl":"10.1134/S1070428025600214","url":null,"abstract":"<p>A series of Betti base derivatives were synthesized by the one-pot three-component DBU-catalyzed condensation of 6-bromonaphthalen-2-ol, qinolin-3-amine, and substituted benzaldehydes under mild reaction conditions and characterized by IR and NMR spectroscopy and mass spectrometry. In vitro α-amylase inhibition assay showed that the synthesized compounds compare in potency with the antidiabetic drug Acarbose, while one of the derivatives (R = 4-CF<sub>3</sub>) showed a superior activity than Ascarbose. In silico docking studies correlated the inhibitory potency with strong binding affinity, particularly for compounds bearing electron-acceptor substituents (F, NO<sub>2</sub>, and CF<sub>3</sub>). The results of the α-amylase assay and molecular docking suggest that the synthesized Betti base derivatives are promising candidates for further development as α-amylase inhibitors, with potential applications in antidiabetic therapies.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1518 - 1525"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242819","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":"A DFT Investigation of Halogen-Substituted Indeno[1,2-b]quinoxaline–Oxazole Derivatives: Insights into Electronic Structure and Reactivity","authors":"Dharmesh Katariya, Gaurav Jadav, Priyank Shah, Umang Patel, Parth Unjiya, Vaishali Rathod, Dhara Desani, Dipen Patel, Vaibhav Bhatt, Jaysukh Markana, Bharat Kataria, Manish Shah, Ranjan Khunt","doi":"10.1134/S1070428025601888","DOIUrl":"10.1134/S1070428025601888","url":null,"abstract":"<p>Density functional theory calculations were used to investigate the structural and electronic properties of three halogen-substituted indeno[1,2<i>-b</i>]quinoxaline–oxazole derivatives: (<i>E</i>)-5-(4-bromophenyl)-2-[2-(7,8-dimethyl-11<i>H</i>-indeno[1,2<i>-b</i>]quinoxalin-11-ylidene)hydrazinyl]oxazole, (<i>E</i>)-5-(4-chlorophenyl)-2-[2-(7,8-dimethyl-11<i>H</i>-indeno[1,2<i>-b</i>]quinoxalin-11-ylidene)hydrazinyl]oxazole, and (<i>E</i>)-2-[2-(7,8-dimethyl-11<i>H</i>-indeno[1,2<i>-b</i>]quinoxalin-11-ylidene)hydrazinyl]-5-(4-fluorophenyl)oxazole. Stable molecular structures for all the three compounds were confirmed through geometry optimization at the RB3LYP/3-21G level of theory. Electronic structure analysis revealed that the frontier molecular orbital energy gaps are strongly influenced by the halogen substituent: Δ<i>E</i><sub>gap</sub> 3.44 eV (Br), 1.79 eV (Cl), and 1.75 eV (F). These variations indicate differences in molecular reactivity, charge transfer properties, and optoelectronic potential. Electrostatic potential (ESP) mapping further elucidated charge distribution patterns, highlighting electrophilic and nucleophilic regions. The findings provide valuable insights into the electronic modulation of the studied quinoxaline–oxazole derivatives, making them promising candidates for optoelectronic and material science applications.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1549 - 1558"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242821","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 of Conjugates of Maleopimaric Acid with Nonsteroidal Anti-inflammatory Drugs","authors":"G. F. Vafina, A. I. Poptsov","doi":"10.1134/S1070428025602365","DOIUrl":"10.1134/S1070428025602365","url":null,"abstract":"<p>New conjugates were synthesized by the reaction of acetylsalicylic acid chlorides, naproxen, ibuprofen, and ketoprofen with 2- and 6-aminomaleopimaric acid derivatives. The structures of the synthesized compounds were proven by IR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, mass spectrometry, and elemental analysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1451 - 1457"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242847","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}
L. A. Baeva, R. M. Nugumanov, R. R. Gataullin, T. R. Nugumanov
{"title":"Synthesis of Functionalized 1,2,3,4-Tetrahydropyridines by the Reaction of 3-[(Propan-2-ylsulfanyl)methyl]pentane-2,4-dione with Anilines","authors":"L. A. Baeva, R. M. Nugumanov, R. R. Gataullin, T. R. Nugumanov","doi":"10.1134/S1070428025601694","DOIUrl":"10.1134/S1070428025601694","url":null,"abstract":"<p>A method for the synthesis of 1,1,1-(6-methyl-1-aryl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanones by the reaction of 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione with anilines in the presence of catalytic amounts of acetic acid was developed. It was found that the reactivity of substituted anilines in the studied reaction depends on the nature and position of the substituent, decreasing in the series: 2,4-Me<sub>2</sub>-С<sub>6</sub>H<sub>3</sub>NH<sub>2</sub> > С<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> 4-Me-С<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> 2-Me-С<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> > 3-Me-С<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> 2-MeO-С<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> > 4-MeC(O)-С<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> 4-Br-С<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1412 - 1421"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242763","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 of Novel Fused Systems Derived from 4-Spiro-Fused 6,7-Dimethoxy-1-(ethoxycarbonyl)dihydroisoquinolines","authors":"A. A. Aghekyan, H. A. Panosyan, A. S. Avagyan","doi":"10.1134/S1070428025601797","DOIUrl":"10.1134/S1070428025601797","url":null,"abstract":"<p>Ethyl esters of 4-spiro-fused 6,7-dimethoxydihydroisoquinoline-1-carboxylatic acids were reduced to the corresponding 1-(hydroxymethyl)tetrahydroisoquinolines. The latter were cyclized with Formalin to form oxazoloisoquinolines, which were then recyclized into tetrahydropyranoisoquinolines by treatment with hydrobromic and concentrated hydrochloric acids. Spiro-fused 1-(hydroxymethyl)isoquinoline-6,7-diols were reacted with dibromoethane to obtain the corresponding dioxinoisoquinolines.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1473 - 1478"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242765","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":"Design, Synthesis, and Anticancer Evaluation of Novel Chalcone Derivatives Bearing a 2-[4-(Pyridin-4-yl)isoxazol-3-yl)benzoxazole Moiety","authors":"P. Durga, C. Hazarathaiah Yadav, L. Eppakayala","doi":"10.1134/S1070428025600226","DOIUrl":"10.1134/S1070428025600226","url":null,"abstract":"<p>A series of novel chalcone derivatives bearing a pyridylisoxazole–benzoxazole moiety were synthesized and evaluated for in vitro anticancer activity against four human cancer cell lines. The majority of the synthesized compounds exhibited significant anticancer potency. Among them, six compounds demonstrated activity comparable to the reference drug etoposide, and one derivative, 1-(3,5-dinitrophenyl)-3-{2-[4-(pyridin-4-yl)isoxazol-3-yl]benzo[<i>d</i>]oxazol-5-yl}prop-2-en-1-one, was found to be more potent than the positive control.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1511 - 1517"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242766","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 of Ketoximes Derived from 5-(2-[(Benzoylamino)-3-methylphenyl]-5-oxopentanoic Acid and Its Methyl Ester and N-tosyl-2-(5-oxopentanoyl)-, N-tosyl-2-(6-oxohexanoyl)-, and N-pivaloyl-2-(5-oxohexanoyl)aniline Acetals","authors":"R. R. Safargalin, R. R. Gataullin","doi":"10.1134/S1070428025601700","DOIUrl":"10.1134/S1070428025601700","url":null,"abstract":"<p>Dimethyl acetals of <i>N</i>-tosyl-2-(5-oxopentanoyl)-, <i>N</i>-tosyl-2-(6-oxohexanoyl)-, and <i>N</i>-pivaloyl-2-(5-oxohexanoyl)anilines have been synthesized. The resulting acetals, as well as 5-(2-[(benzoylamino)-3-methylphenyl]-5-oxopentanoic acid and its methyl ester were reacted with hydroxylamine to obtain the corresponding ketoximes as <i>syn</i>/<i>anti</i> isomer mixtures.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1399 - 1407"},"PeriodicalIF":0.9,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145242817","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}