Russian Chemical Bulletin最新文献

{"title":"Complexation of bis(aza-18-crown-6)-containing dibenzylidenecyclopentanone with alkali and alkaline-earth metal cations: specific features and photoinduced recoordination in the complexes","authors":"V. V. Volchkov, M. N. Khimich, M. Ya. Melnikov, O. A. Alatortsev, F. E. Gostev, I. V. Shelaev, V. A. Nadtochenko, R. O. Starostin, M. V. Fomina, A. E. Egorov, A. Ya. Freidzon, S. P. Gromov","doi":"10.1007/s11172-024-4274-y","DOIUrl":"https://doi.org/10.1007/s11172-024-4274-y","url":null,"abstract":"<p>An analysis of the results of time-resolved transient S₁→S_<i>n</i> absorption spectroscopy studies and quantum chemical calculations of the dye (2<i>E</i>,5<i>E</i>)-2,5-bis[4-(1,4,7,10,13-pentaoxa-16-azacyclooctadecane-16-yl)benzylidene]cyclopentanone (<b>1</b>) and its metal complexes confirm the generality of the phenomenon of photoinduced recoordination of metal cations in the complexes of bis(aza-18-crown-6)-containing derivatives of the dibenzylidenecyclobutanone (dibenzylidenecyclopentanone) series. The results obtained confirmed the existence of the first stage of photoinduced recoordination of metal cations in the <b>1</b> • (Mⁿ⁺)₂ (M = Ba²⁺, Ca²⁺, K⁺) complexes which completes within a few hundreds of femtoseconds. The process involves cleavage of the N—M bond followed by displacement of the metal cation from its equilibrium position in the azacrown ether cavity and by transformation of the “axial” conformation of the complex to “equatorial” one. It was demonstrated that the barrier photoinduced recoordination of the cation in the <b>1</b> • (Ba²⁺)₂ complex is accompanied by the change of the type of the solvation shell of the crowned Ba²⁺ cation in the following order: (2+1)MeCN, (3+1)MeCN, 4MeCN. In a low-temperature butyronitrile glassy matrix at 77 K, the photoinduced recoordination is completely suppressed. The Mg²⁺, Li⁺, and Na⁺ cations can form not only the inclusion complexes, but also the 1: 3 complexes ((M^<i>n</i>+) • <b>1</b> • (M^<i>n</i>+)₂) of moderate stability through additional coordination to the carbonyl group of the dye. The radii, <i>r</i>_S, of solvates of different-stoichiometry complexes containing the same metal cation determined from the data of anisotropy decay kinetics of S₁→S_<i>n</i> absorption are about 9.2 Å for <b>1</b> • (Mg²⁺)₂ and nearly 11.5 Å for Mg²⁺ • <b>1</b> • (Mg²⁺)₂.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784907","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":"Influence of the sulfonyl group on the biological activity of 2-sulfonarylhydrazinylidene 1,3-dicarbonyl compounds","authors":"N. A. Elkina, O. G. Khudina, Ya. V. Burgart, E. V. Shchegolkov, O. G. Serebryakova, E. V. Rudakova, N. P. Boltneva, N. V. Kovaleva, G. F. Makhaeva, N. A. Gerasimova, N. P. Evstigneeva, V. I. Saloutin","doi":"10.1007/s11172-024-4294-7","DOIUrl":"https://doi.org/10.1007/s11172-024-4294-7","url":null,"abstract":"<p>The azo-coupling reaction of aryldiazonium chlorides containing a sulfone fragment with ethyl (trifluoro)acetylacetates and acetylacetone led to 2-sulfonarylhydrazinylidene 1,3-dicarbonyl compounds. According to NMR spectroscopy, 2-sulfonarylhydrazinylidene 3-oxoesters exist in solutions as <i>Z</i>-isomers. Micromolar inhibitors of three serine esterases, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and carboxylesterase (CES), were found among the synthesized trifluoromethyl-substituted 3-oxoesters. A nanomolar BChE inhibitor was identified among the trifluoromethyl-substituted 1,3-diketone derivatives exhibiting selectivity towards BChE in combination with radical-scavenging activity. 3-Oxoesters with moderate activity against pathogenic fungi of the <i>T. mentagrophytes</i> strain were revealed.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784901","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":"3,6-Disubstituted derivatives of 1,2,4,5-tetrazine with pyridinyl amidine moieties and condensed systems on their basis: synthesis, docking, and antibacterial activity","authors":"R. I. Ishmetova, N. K. Ignatenko, N. A. Gerasimova, D. V. Belyaev, I. I. Butorin, O. A. Konovalova, E. E. Khramtsova, D. V. Dianov, N. P. Evstigneeva, D. V. Vakhrusheva, S. Yu. Krasnoborova, N. V. Zilberberg, N. V. Kungurov, G. L. Rusinov, V. N. Charushin","doi":"10.1007/s11172-024-4286-7","DOIUrl":"https://doi.org/10.1007/s11172-024-4286-7","url":null,"abstract":"<p>New 3,6-disubstituted 1,2,4,5-tetrazine derivatives with pyridyl-substituted amidine moieties, as well as [1,2,4]triazolo[1,5-<i>b</i>][1,2,4,5-tetrazines and bis[1,2,4]triazolo-[1,5-<i>b</i>:1,5-<i>f</i>][1,2,4,5]tetrazines on their basis were synthesized. The obtained compounds were screened for activity against <i>Neisseria gonorrhoeae</i> and <i>Mycobacterium tuberculosis</i>. Compounds with pronounced antibacterial activity were detected. Docking was performed to determine a possible antibacterial effect of the compounds.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784880","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":"Benzyl complexes of rare earth metals","authors":"D. M. Lyubov, A. A. Trifonov","doi":"10.1007/s11172-024-4271-1","DOIUrl":"https://doi.org/10.1007/s11172-024-4271-1","url":null,"abstract":"<p>Data on the synthesis, structure, and reactivity of benzyl complexes of rare earth elements in the oxidation state +3 are integrated and analyzed. A variety of methods for the synthesis of homoleptic tris(benzyl) derivatives and heteroleptic mono- and bis(benzyl) complexes containing spectator ligands of various nature and denticity are considered. The attention is focused on the structure of Ln^III benzyl derivatives in the crystalline state. It is shown that the mode of coordination of the benzyl ligand to Ln³⁺ ions depends on the ionic radius and steric congestion of the metal center, as well as on the ligand nature and can vary from κ¹-C_α- to poly-<i>hapta</i>-coordination due to the non-valent interactions of the metal center with the <i>ipso-</i> and <i>ortho</i>-atoms of the aromatic ring.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784868","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":"Isobornylchalcones and flavones derived from them: synthesis and antioxidant activity","authors":"S. A. Popova, M. V. Krylova, E. V. Pavlova, O. G. Shevchenko, I. Yu. Chukicheva","doi":"10.1007/s11172-024-4295-6","DOIUrl":"https://doi.org/10.1007/s11172-024-4295-6","url":null,"abstract":"<p>Methoxychalcones containing the NMe₂, 3,4-(OMe)₂, 3,4,5-(OMe)₃, and isobornyl substituents in the B ring were synthesized from 1,3-dihydroxy-4-(1,7,7-trimethylbicyclo-[2.2.1]hept-<i>exo</i>-2-yl)benzene and 1,4-dihydroxy-3-(1,7,7-trimethylbicyclo[2.2.1]hept-<i>exo</i>-2-yl)benzene. Oxidative cyclization of the new isobornylchalcones afforded flavones bearing the 1,7,7-trimethylbicyclo[2.2.1]hept-<i>exo</i>-2-yl moiety. The erythrotoxicity, membrane-protective, and antioxidant activity of the synthesized compounds were evaluated in <i>in vitro</i> models including the model of oxidative hemolysis of mammalian erythrocytes initiated by H₂O₂ or 2,2′-azobis-(2-amidinopropane) dihydrochloride. All the chalcones studied and most flavones possessed good hemocompatibility and high antioxidant activity. The promise of further research into the synthesis of effective pharmacological substances based on the title compounds was demonstrated.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784906","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":"Rearrangement of 3-(bromomethyl)quinoxalin-2(1H)-ones when exposed to 2-aminopyridines as a new method for the synthesis of 2-(imidazo[1,2-a]pyridin-2-yl)benzimidazoles","authors":"N. A. Zhukova, D. S. Perevalova, V. V. Syakaev, T. N. Beschastnova, A. T. Gubaidullin, O. G. Sinyashin, V. A. Mamedov","doi":"10.1007/s11172-024-4287-6","DOIUrl":"https://doi.org/10.1007/s11172-024-4287-6","url":null,"abstract":"<p>A new efficient method was developed for the synthesis of 2-(imidazo[1,2-<i>a</i>]pyridin-2-yl)benzimidazoles based on the Mamedov rearrangement. The key step of the synthesis involves the acid-catalyzed rearrangement of spiroquinoxalinone derivatives as intramolecular cyclization products of 2-amino-1-[(quinoxalin-2(1<i>H</i>)-on-3-yl]methyl)pyridinium salts, which are generated by the modified Chichibabin reaction.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784881","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":"Transformation routes of tetrafluoroflavones in the reactions with aliphatic amines","authors":"M. A. Panova, K. V. Shcherbakov, K. A. Chernyakov, N. A. Gerasimova, N. P. Evstigneeva, Ya. V. Burgart, V. I. Saloutin","doi":"10.1007/s11172-024-4276-9","DOIUrl":"https://doi.org/10.1007/s11172-024-4276-9","url":null,"abstract":"<p>Routes of modification of 5,6,7,8-tetrafluoro-3-methoxycarbonyl-2-(4-methoxyphenyl)-4<i>H</i>-chromen-4-one and its decarboxylated analogs in the reactions with aliphatic amines were studied and the biological activity of both the starting compounds and the products was tested. It was found that 5,6,7,8-tetrafluoro-3-methoxycarbonyl-2-(4-methoxyphenyl)-4<i>H</i>-chromen-4-one under the action of primary amines underwent the flavone-coumarin rearrangement through the addition of the amine at the C(2) atom. 7-Amino-substituted flavones were formed as by-products in the reactions with methyl- and benzylamines and as major products in the reactions with pyrrolidine. The process of nucleophilic aromatic substitution at the C(7) atom becomes a key one in the reactions of decarboxylated tetrafluoroflavones with primary amines and pyrrolidine. Mechanisms for the studied transformations were proposed. The starting tetrafluoroflavones were found to exhibit high antifungal activity, while antigonorrheal agents were revealed among the products of their transformations.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784871","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":"Modified 2,3-bis(thienyl)quinoxaline fluorophores as potential chemosensors","authors":"T. N. Moshkina, A. E. Kopotilova, D. A. Gazizov, M. I. Valieva, E. S. Starnovskaya, A. A. Kalinichev, D. S. Kopchuk, E. V. Nosova, V. N. Charushin","doi":"10.1007/s11172-024-4292-9","DOIUrl":"https://doi.org/10.1007/s11172-024-4292-9","url":null,"abstract":"<p>2,3-Bis[5-(pyren-1-yl)thiophen-2-yl]quinoxalines and 2,3-bis{5-[4-(9<i>H</i>-carbazol-9-yl)phenyl]thiophen-2-yl}pyrazino[2,3-<i>f</i>][1,10]phenanthroline were synthesized. One- and two-photon absorption and emission of the compounds were studied, the cross sections of the two-photon absorption were found to be equal to 101–476 GM in THF. Fluorescent responses of pyrene-containing fluorophores and dipyrido-annelated quinoxaline to nitroaromatic compounds and metal cations, respectively, were investigated.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784887","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 ipidacrine with oxa/azaheterocycles and their potential as agents for the treatment of Alzheimer’s disease","authors":"O. G. Khudina, M. V. Grishchenko, G. F. Makhaeva, Ya. V. Burgart, N. P. Boltneva, M. V. Goryaeva, N. V. Kovaleva, E. V. Rudakova, S. O. Bachurin, V. I. Saloutin","doi":"10.1007/s11172-024-4293-8","DOIUrl":"https://doi.org/10.1007/s11172-024-4293-8","url":null,"abstract":"<p>Ipidacrine conjugates were synthesized by alkylation of 4-hydroxycoumarin, dihydrofuro[3,4-<i>c</i>]pyridine, bipyridine, and azolo[1,5-<i>a</i>]pyrimidines with 2-chloro-<i>N</i>-(hexahydrocyclopenta[<i>b</i>]quinolin-9-yl)acetamide. Their isomeric structure was determined by NMR spectroscopy. Heterocycles containing ambident N,O-nucleophilic centers underwent alkylation at the oxygen atom, while in the presence of alternative carboxy and hydroxy functions, the alkylation occurred with the formation of an ester derivative. The study of the esterase profile, inhibitory effect on β-amyloid self-aggregation, as well as antioxidant activity of the conjugates, showed that coumarin derivatives are promising for the development of butyrylcholinesterase inhibitors, whereas conjugates of azolo[1,5-<i>a</i>]-pyrimidines are promising in the search for β-amyloid self-aggregation inhibitors.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784888","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":"Effects of the structure of primary nitroalkanes and reaction conditions on the selectivity of acylamination of arenes in polyphosphoric acid","authors":"A. V. Aksenov, I. Yu. Grishin, D. A. Aksenov, Yu. I. Grishin, I. V. Aksenova, N. A. Aksenov","doi":"10.1007/s11172-024-4277-8","DOIUrl":"https://doi.org/10.1007/s11172-024-4277-8","url":null,"abstract":"<p>The mechanism of acylamination of arenes with nitroalkanes in polyphosphoric acid has been clarified. The influence of the concentration of polyphosphoric acid, the structure of the starting compounds, and temperature on the result of the Beckmann rearrangement, which makes it possible to shift the reaction towards either benzamides or anilides, has been assessed.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784873","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}