{"title":"Alkynylcarbenes: generation, properties, and application in organic synthesis","authors":"V. D. Gvozdev, K. N. Shavrin, M. P. Egorov","doi":"10.1007/s11172-024-4648-1","DOIUrl":"10.1007/s11172-024-4648-1","url":null,"abstract":"<div><p>The present review systematizes the currently known data on the methods for generating various types of alkynylcarbenes, information on their structure, properties, and reactions. Special attention is given to such approaches to alkynylcarbenes as decomposition of the corresponding diazo compounds and arylsulfonylhydrazone salts, photolysis of 3<i>H</i>-pyrazoles, thermolysis of aziridinylimines, as well as numerous processes that involve based-induced elimination reactions. Data on the structure and reactivity studies of a number of alkynylcarbenes under matrix isolation conditions and the examples of application of these intermediates for the directed introduction of the alkynyl moieties into organic compounds of different classes <i>via</i> (1+2)-cycloaddition and insertion reactions are presented.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1541 - 1575"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164357","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}
Yu. N. Bubnov, A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, S. V. Baranin
{"title":"Synthesis of functionalized hydroxymethylene-containing bisorganophosphorus acids","authors":"Yu. N. Bubnov, A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, S. V. Baranin","doi":"10.1007/s11172-024-4667-y","DOIUrl":"10.1007/s11172-024-4667-y","url":null,"abstract":"<div><p>Convenient syntheses of functionalized bisorganophosphorus acids and their derivatives containing hydroxymethylene moieties have been developed. Trimethylsilyl esters of trivalent phosphorus acids react with acyl chlorides to give new hydroxymethylene-substituted functionalized bisorganophosphorus acids containing P—C—P units. The resulting compounds are structural analogs of pharmaceutical agents used to treat various diseases. They are also of interest as promising biologically active substances and effective polydentate ligands.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1822 - 1837"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164370","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}
R. A. Kushnazarova, A. B. Mirgorodskaya, E. N. Nikitin, L. Ya. Zakharova
{"title":"Micellar systems based on syntanols ALM: physicochemical properties and application as adjuvants in herbicide formulations","authors":"R. A. Kushnazarova, A. B. Mirgorodskaya, E. N. Nikitin, L. Ya. Zakharova","doi":"10.1007/s11172-024-4663-2","DOIUrl":"10.1007/s11172-024-4663-2","url":null,"abstract":"<div><p>A series of domestic syntanols ALM of the general formula C<sub><i>n</i></sub>H<sub>(2<i>n</i>+1)</sub>O(C<sub>2</sub>H<sub>4</sub>O)<sub><i>m</i></sub> and different hydrophilic-lipophilic balance (HLB) were tested to evaluate their potential as adjuvants in herbicide formulations. A comparative analysis of aggregation behavior, surface activity, and solubility of these syntanols and their commercially available foreign analogue Brij®35 was carried out. Using spectrophotometric method, it was shown that syntanol ALM-7 has the greatest solubilizing effect on hydrophobic compounds. Using dandelion leaves as an example, it was demonstrated that, among the tested compounds, syntanols ALM-2 and ALM-7 provided the most efficient transport of the herbicide dicamba to target weeds.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1786 - 1792"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164349","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":"Mono-, di-, and triazidation of 1,3,5-trifluoro-2,4,6-triiodobenzene","authors":"I. K. Yakushchenko, S. V. Chapyshev","doi":"10.1007/s11172-024-4658-z","DOIUrl":"10.1007/s11172-024-4658-z","url":null,"abstract":"<div><p>Conditions for mono-, di-, and triazidation of 1,3,5-trifluoro-2,4,6-triiodobenzene with sodium azide were developed varying solvents, temperature, and molar ratio of reactants to furnish 1-azido-3,5-difluoro-2,4,6-triiodobenzene, 1,3-diazido-5-fluoro-2,4,6-triiodobenzene, and 1,3,5-triazido-2,4,6-triiodobenzene, which can be used as precursors for photochemical synthesis of triiodinated mono-, di-, and trinitrenes.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1749 - 1752"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145163447","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}
E. A. Samoilenko, K. A. Koshenskova, O. V. Selitskaya, L. S. Razvorotneva, F. M. Dolgushin, O. B. Bekker, V. O. Shender, I. L. Eremenko, I. A. Lutsenko
{"title":"Antiphytopathogenic and anticancer activity of CuII and CoII furancarboxylate complexes","authors":"E. A. Samoilenko, K. A. Koshenskova, O. V. Selitskaya, L. S. Razvorotneva, F. M. Dolgushin, O. B. Bekker, V. O. Shender, I. L. Eremenko, I. A. Lutsenko","doi":"10.1007/s11172-024-4669-9","DOIUrl":"10.1007/s11172-024-4669-9","url":null,"abstract":"<div><p>The trinuclear complex [Co<sub>3</sub>(3-fur)<sub>6</sub>(phen)<sub>2</sub>] (<b>1</b>; 3-fur is a 3-furancarboxylate anion, phen is 1,10-phenanthroline) was obtained by the slow diffusion of a methanol solution of cobalt(<span>ii</span>) furoate and an acetonitrile solution of 1,10-phenanthroline. The structure of complex <b>1</b> was established by X-ray diffraction analysis. According to the X-ray diffraction data, the Co<sup>II</sup> atoms are in a linear arrangement in the metal core and adopt an octahedral coordination environment formed by nitrogen and oxygen atoms, {CoO<sub>4</sub>N<sub>2</sub>} and {CoO<sub>6</sub>}, and the phenanthroline molecules are coordinated in chelate fashion to the terminal Co<sup>II</sup> atoms. The crystal packing of <b>1</b> is stabilized by π—π interactions between the phenanthroline aromatic system and the furan rings of the adjacent molecules. The biological activity of complexes <b>1</b> and [Cu(2-fur)<sub>2</sub>(phen)] was evaluated <i>in vitro</i> against phytopathogenic gram-positive and gram-negative bacteria and the model mycobacterium strain <i>Mycolicibacterium smegmatis</i>. The cytotoxic effects were assessed against SKOV3 human ovarian adenocarcinoma cells and HDF primary human dermal fibroblast cells.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1847 - 1855"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164360","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":"Mesomorphism of salicylideneaniline luminophores. X-ray diffraction and differential scanning calorimetry studies of 4-ethoxy-4′-heptylsalicylideneaniline","authors":"L. G. Kuz’mina, P. Kalle, B. M. Bolotin","doi":"10.1007/s11172-024-4657-0","DOIUrl":"10.1007/s11172-024-4657-0","url":null,"abstract":"<div><p>The structure and photothermal properties of the mesomorphic Schiff base 4-ethoxy-4′-heptylsalicylideneaniline (<b>1</b>) were studied by X-ray diffraction analysis and differential scanning calorimetry. Compound <b>1</b> exhibits photochromism and displays luminescence in the solid state and in a mesophase. The crystal unit cell of <b>1</b> contains two crystallographically independent molecules (A and B) adopting significantly different conformations. The molecules have a benzoid configuration of the bonds; in both molecules, the active proton was unambiguously located at the oxygen atom. According to the DSC analysis, compound <b>1</b> exhibits enantiotropic mesomorphism with a broad temperature range of mesophase (48.5–96.6 °C) and a low melt—mesophase phase transition temperature. In the crystal, the molecules form centrosymmetric tetramers stacked in the B⋯A⋯A⋯B order. Two central molecules (A⋯A) of the tetramer are linked together through a π⋯π-stacking interaction. Interactions between the B⋯A molecules (and the A⋯B molecules) occur through two C—H⋯π-system secondary bonds involving both benzene rings. The crystal packing consists of alternating loosely packed aliphatic layers and closely packed aromatic layers enriched with functional groups.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1740 - 1748"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164473","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}
P. A. Panchenko, A. S. Polyakova, V. A. Perevozchikov, O. A. Fedorova
{"title":"Fluorescent PET chemosensor for copper(ii) cations based on a 4-methoxy-1,8-naphthalimide derivative containing an iminodiacetate receptor fragment","authors":"P. A. Panchenko, A. S. Polyakova, V. A. Perevozchikov, O. A. Fedorova","doi":"10.1007/s11172-024-4659-y","DOIUrl":"10.1007/s11172-024-4659-y","url":null,"abstract":"<div><p>A new fluorescent chemosensor based on 1,8-naphthalimide containing an iminodiacetate receptor fragment (N(CH<sub>2</sub>COOH)<sub>2</sub>) and capable of selectively detecting copper(<span>ii</span>) cations in acetonitrile solution was synthesized. The sensor demonstrates a low level of fluorescence in the absence of metal cations, which is related to photoinduced electron transfer (PET) from the receptor to the naphthalimide chromophore. Binding of Cu<sup>2+</sup> ions leads to the formation of two complexes with a metal: ligand ratio of 2: 1 and 1: 1 ([Cu<sub>2</sub>L]<sup>2+</sup> and CuL, respectively) and is accompanied by fluorescence enhancement due to the suppression of the PET process in [Cu<sub>2</sub>L]<sup>2+</sup>. Spectrofluorimetric titration was used to determine the stability constants of CuL and [Cu<sub>2</sub>L]<sup>2+</sup> particles, which were found to be 7.9•10<sup>6</sup>±2.6•10<sup>6</sup> L mol<sup>−1</sup> and 1.0•10<sup>12</sup>±0.3•10<sup>12</sup> L<sup>2</sup> mol<sup>−2</sup>, respectively. The observed spectral effects were interpreted using the results of quantum chemical calculations.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 6","pages":"1753 - 1760"},"PeriodicalIF":1.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145164474","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. V. Pugachev, T. A. Khamzin, I. I. Svintsova, R. M. Khaziev, M. N. Agafonova, O. V. Bondar, O. I. Gnezdilov, Yu. G. Shtyrlin
{"title":"Synthesis and antitumor activity of β-glucosides bearing moieties of pyridoxine derivative and 4-methylbenzoic acid","authors":"M. V. Pugachev, T. A. Khamzin, I. I. Svintsova, R. M. Khaziev, M. N. Agafonova, O. V. Bondar, O. I. Gnezdilov, Yu. G. Shtyrlin","doi":"10.1007/s11172-025-4641-3","DOIUrl":"10.1007/s11172-025-4641-3","url":null,"abstract":"<div><p>A series of new β-glucosides bearing pyridoxine-based aglycones and 4-methylbenzoyl moiety at the O(6) atom was synthesized. Cytotoxicity of the synthesized compounds was evaluated <i>in vitro</i> against four human tumor (MCF-7, HCT-116, PC-3, MDA-MB-231) and two human conditionally normal (Chang Liver, MSC) cell lines using camptothecin, doxorubicin, and saccharumoside-B as the reference drugs. The structure—antitumor activity relationships were established.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 5","pages":"1451 - 1466"},"PeriodicalIF":1.7,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165721","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}
E. S. Filatova, O. V. Fedorova, I. G. Ovchinnikova, V. I. Uvarova, E. V. Khvatov, M. K. Kaleda, L. I. Kozlovskaya, G. L. Rusinov, V. N. Charushin
{"title":"Podands with phthalimide and dihydro(azolo)pyrimidine or pyrazolopyridine moieties, their cytotoxicity and antiviral activity","authors":"E. S. Filatova, O. V. Fedorova, I. G. Ovchinnikova, V. I. Uvarova, E. V. Khvatov, M. K. Kaleda, L. I. Kozlovskaya, G. L. Rusinov, V. N. Charushin","doi":"10.1007/s11172-025-4625-3","DOIUrl":"10.1007/s11172-025-4625-3","url":null,"abstract":"<div><p>Podands bearing phthalimide and dihydro(azolo)pyrimidine or pyrazolopyridine moieties at the ends of the oligooxyethylene spacer were synthesized. The cytotoxicity and antiviral activity against the SARS-CoV-2 coronavirus of the synthesized compounds were evaluated, and these compounds were assessed as potential inhibitors of the main protease (Mpro) of SARS-CoV-2 compared to compounds lacking this podand moiety.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 5","pages":"1300 - 1311"},"PeriodicalIF":1.7,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165344","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. S. Gushchina, Yu. L. Kuznetsova, M. N. Egorikhina, E. A. Levicheva, L. L. Semenycheva
{"title":"Alkylborane—p-quinone system in the synthesis of collagen and vinylpyrrolidone copolymers as a basis of materials for regenerative medicine","authors":"K. S. Gushchina, Yu. L. Kuznetsova, M. N. Egorikhina, E. A. Levicheva, L. L. Semenycheva","doi":"10.1007/s11172-025-4643-1","DOIUrl":"10.1007/s11172-025-4643-1","url":null,"abstract":"<div><p>The grafted polymerization of <i>N</i>-vinylpyrrolidone onto collagen in the presence of tributylborane and a number of <i>p</i>-quinones (<i>p</i>-benzoquinone, <i>p</i>-naphthoquinone, 2,5-di-<i>tert</i>-butyl-<i>p</i>-benzoquinone, and duroquinone) was studied. The trialkylborane—<i>p</i>-quinone system allows one to form cross-linked copolymers due to a combination of two polymerization routes: “<i>grafting from</i>” and “<i>grafting to</i>.” Grafted poly-<i>N</i>-vinylpyrrolidone has high molecular weights and a high degree of polydispersity, which depend on the structure of the <i>p</i>-quinone used. An MTT assay of cytotoxicity shows that the copolymer extracts exhibit pronounced toxicity, which decreases when diluting with a growth medium to the appearance of the stimulating effect on the cell growth.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 5","pages":"1476 - 1486"},"PeriodicalIF":1.7,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145165349","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}