O. N. Grebyonkina, O. A. Banina, R. V. Rumyantsev, D. R. Baidamshina, A. I. Kolesnikova, O. M. Lezina, S. A. Rubtsova
{"title":"Synthesis of new chiral arylsulfonamides based on carane amino alcohols","authors":"O. N. Grebyonkina, O. A. Banina, R. V. Rumyantsev, D. R. Baidamshina, A. I. Kolesnikova, O. M. Lezina, S. A. Rubtsova","doi":"10.1007/s11172-024-4345-0","DOIUrl":"10.1007/s11172-024-4345-0","url":null,"abstract":"<div><p>New optically active arylsulfonamides, including carane-containing streptocide analogs, were synthesized by the reaction of carane amino alcohols with tosyl- and <i>N</i>-acetylsulfanilyl chlorides. Sulfonamide, which was prepared based on (–)-4β-amino-3α-hydroxy-<i>cis</i>-carane, was studied by X-ray diffraction. The synthesized sulfonamides and the starting amino alcohols were evaluated for antimicrobial activity.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2238 - 2247"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267594","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. Yu. Zyryanova, I. A. Utepova, A. A. Musikhina, N. P. Boltneva, N. V. Kovaleva, E. V. Rudakova, O. G. Serebryakova, G. F. Makhaeva, M. A. Kiskin, V. F. Lazarev, L. S. Kuznetsova, I. V. Guzhova, O. N. Chupakhin
{"title":"1,1′-Disubstituted azinylferrocenes: synthesis, antiaggregation and antioxidant activity","authors":"E. Yu. Zyryanova, I. A. Utepova, A. A. Musikhina, N. P. Boltneva, N. V. Kovaleva, E. V. Rudakova, O. G. Serebryakova, G. F. Makhaeva, M. A. Kiskin, V. F. Lazarev, L. S. Kuznetsova, I. V. Guzhova, O. N. Chupakhin","doi":"10.1007/s11172-024-4364-x","DOIUrl":"10.1007/s11172-024-4364-x","url":null,"abstract":"<div><p>An approach to the synthesis of derivatives of unsymmetric 1,1′-disubstituted azinylferrocenes containing phenol fragments was proposed. It was found that the introduction of the quinoline or 2,2′-bipyridine moiety increases the <i>E/Z</i> selectivity of the reaction. The monosubstituted acetylferrocene produces the products of the pinacoline rearrangement due to the McMurry coupling, whereas only 1-azinyl-1′-{1-[(4-hydroxyphenyl)-phenylmethylene]ethyl}ferrocenes were formed in the reaction with 1-azinyl-1′-acetyl-ferrocenes. The high antioxidant activity of the synthesized compounds in the ABTS and FRAP assays and high inhibitory activity against self-aggregation of β-amyloid (1–42) was shown. Cytotoxic activity of these compounds was studied on human breast cancer cells (MCF7), non-small-cell lung cancer cells (A549), colorectal cancer cells (DLD-1), and normal dermal fibroblasts (DF-2).</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2408 - 2421"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269644","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. Goryaeva, M. A. Ezhikova, Ya. V. Burgart, M. S. Kustova, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin
{"title":"Synthesis and spatial structure of 3,7-dihydroxy-7-(trifluoromethyl)hexahydropyrrolo[1,2-a]pyrimidines","authors":"M. V. Goryaeva, M. A. Ezhikova, Ya. V. Burgart, M. S. Kustova, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin","doi":"10.1007/s11172-024-4350-3","DOIUrl":"10.1007/s11172-024-4350-3","url":null,"abstract":"<div><p>A characteristic feature of the three-component cyclization of ethyl trifluoropyruvate and methyl ketones with 1,3-diamino-2-propanol is the formation of 8a-alkyl(phenyl)-3,7-dihydroxy-7-(trifluoromethyl)hexahydropyrrolo[1,2-<i>a</i>]pyrimidin-6(2<i>H</i>)-ones as one, two, or three diastereomers, depending on the methyl ketone component. The structures of the new heterocycles were established using the data of X-ray diffraction and <sup>1</sup>H and <sup>13</sup>C NMR spectra, including 2D <sup>1</sup>H—<sup>13</sup>C HSQC, HMBC, <sup>1</sup>H—<sup>1</sup>H COSY, and NOESY experiments.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2280 - 2290"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269639","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}
T. V. Glukhareva, T. A. Kalinina, K. L. Obydennov, O. A. Vysokova, P. A. Slepukhin
{"title":"Synthesis and fungicidal activity evaluation of 5-benzylidene-5H-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazines","authors":"T. V. Glukhareva, T. A. Kalinina, K. L. Obydennov, O. A. Vysokova, P. A. Slepukhin","doi":"10.1007/s11172-024-4361-0","DOIUrl":"10.1007/s11172-024-4361-0","url":null,"abstract":"<div><p>A series of 5-benzylidene-5<i>H</i>-[1,2,3]triazolo[5,1-<i>b</i>][1,3,4]thiadiazines were synthesized by the reaction of benzaldehyde 1,2,3-thiadiazol-5-ylhydrazones with a-bromo-4-chloroacetophenone and chloroacetone in the presence of triethylamine. The key steps of the reaction are the Dimroth rearrangement of the 1,2,3-thiadiazole ring, the formation of 6,7-dihydro-5<i>H</i>-[1,2,3]triazolo[5,1-<i>b</i>][1,3,4]thiadiazines, and the transformation of the thiadiazine ring giving 5-arylidene-5<i>H</i>-[1,2,3]triazolo[5,1-<i>b</i>][1,3,4]thiadiazines. It was demonstrated that 6,7-dihydro-5<i>H</i>-[1,2,3]triazolo[5,1-<i>b</i>][1,3,4]thiadiazines, which do not undergo the transformation in the presence of triethylamine, can be transformed into 5-arylidene-5<i>H</i>-[1,2,3]triazolo[5,1-<i>b</i>][1,3,4]thiadiazines using sodium hydroxide. The reaction is accompanied by the saponification of the ethoxycarbonyl substituent. A number of the synthesized compounds were tested for fungicidal activity against four strains of phytopathogenic fungi and the oomycete <i>P. infestans</i>. Compound <b>5n</b> exhibits a moderate inhibitory effect (56.31±0.13%) on the growth of <i>P. infestans</i>.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2385 - 2393"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267590","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":"Hydrazine complexes with formic acid formed in the N2H4—HCOOH—HCOO− system in the presence of KOBut—DMSO superbase: a quantum chemical study","authors":"V. B. Orel, G. R. Gnatovskiy, N. M. Vitkovskaya","doi":"10.1007/s11172-024-4340-5","DOIUrl":"10.1007/s11172-024-4340-5","url":null,"abstract":"<div><p>Hydrazine complexes with formic acid, free formate ion, and a potassium formate complex 5DMSO · K<sup>+</sup>HCOO<sup>−</sup> formed in the system N<sub>2</sub>H<sub>4</sub>—HCOOH—K<sup>+</sup>HCOO<sup>−</sup>— DMSO were studied. The possibility for hydrazine formylation to occur was assessed. According to calculations, a [N<sub>2</sub>H<sub>6</sub>(HCOO)<sub>3</sub>]<sup>−</sup> complex is formed in the system in question. The calculated kinetic and thermodynamic characteristics suggest that hydrazine formylation can occur in this complex. The reaction is reversible; as a consequence, the reaction medium can contain both the [N<sub>2</sub>H<sub>6</sub>(HCOO)<sub>3</sub>]<sup>−</sup> complex and formylhydrazine. All calculations were carried out using the B2PLYP-D2/6-311+G**//B3LYP/6-31+G* approach with inclusion of solvation effects in terms of the IEFPCM continuum model with DMSO as solvent and with explicit inclusion of the nearest solvation shell of the potassium cation (five DMSO molecules).</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2191 - 2198"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267627","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. S. Mikhailov, N. S. Gudim, L. V. Mikhalchenko, M. I. Knysh, E. A. Knyazeva, O. A. Rakitin
{"title":"Dye-sensitized solar cells based on D—A—π—A′ structures with a 4H-cyclopenta[2,1-b:3,4-b′]dithiophene fragment containing branched alkyl groups","authors":"M. S. Mikhailov, N. S. Gudim, L. V. Mikhalchenko, M. I. Knysh, E. A. Knyazeva, O. A. Rakitin","doi":"10.1007/s11172-024-4341-4","DOIUrl":"10.1007/s11172-024-4341-4","url":null,"abstract":"<div><p>Two new dyes were obtained; their D—A—π—A′ structure included benzo[<i>d</i>][1,2,3]-thiadiazole as an internal acceptor (A), a cyanoacrylic acid residue as a terminal anchor acceptor (A′), a 4<i>H</i>-cyclopenta[2,1-<i>b</i>:3,4-<i>b</i>′]dithiophene π-spacer with branched alkyl groups, and 2,3-dihydroindole condensed with carbocycles as a donor. The optical and electrochemical characteristics of the obtained dyes were determined, and solar cells based on them were assembled. The power conversion efficiency reached 3.05% for a device based on the dye containing a 2,3,4,4a,9,9a-hexahydro-1<i>H</i>-carbazole donor moiety. The relatively low value of photovoltaic efficiency is likely due to excessive steric effects that are demonstrated by the branched alkyl groups when the dyes are sorbed onto the TiO<sub>2</sub> surface, which leads to an insufficient concentration of the dye on the electrode surface, resulting in a decrease in the quantity of absorbed photons.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2199 - 2210"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267575","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. L. Makhamatkhanova, E. Yu. Bulykina, T. V. Tyumkina
{"title":"Atom-economical addition of aldehydes to 3-alkyl-1H-phospholane oxides","authors":"A. L. Makhamatkhanova, E. Yu. Bulykina, T. V. Tyumkina","doi":"10.1007/s11172-024-4357-9","DOIUrl":"10.1007/s11172-024-4357-9","url":null,"abstract":"<div><p>Solvent- and catalyst-free reaction of 3-R-1<i>H</i>-phospholane oxides with aldehydes at 20–22 °C for 30 min gave the mixtures of four diastereomers of the corresponding 3-substituted 1-hydroxymethyl-1<i>H</i>-phospholane oxides in 85–98% yields.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2332 - 2338"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267585","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. Ushakova, V. V. Fedotov, I. I. Butorin, E. N. Ulomsky, V. L. Rusinov
{"title":"Benzothiazolo[3,2-a]pyrimidines and benzothiazolo[3,2-a]purines: synthesis and bioactivity prediction","authors":"A. A. Ushakova, V. V. Fedotov, I. I. Butorin, E. N. Ulomsky, V. L. Rusinov","doi":"10.1007/s11172-024-4355-y","DOIUrl":"10.1007/s11172-024-4355-y","url":null,"abstract":"<div><p>An efficient strategy for the synthesis of benzothiazolo[3,2-<i>a</i>]pyrimidine and benzothiazolopurine derivatives was developed. The synthesis of benzothiazolopyrimidines involves cyclization of 2-aminobenzothiazole with bis(trichlorophenyl) malonate, nitration, chlorodeoxygenation, and reaction of the chlorinated derivative with secondary amines. Benzimidazolopyrimidines were transformed to benzo[4,5]thiazolo[3,2-<i>a</i>]purines by one-pot reduction of the nitro group followed by imidazole ring closure. The synthesized compounds were characterized by physicochemical analysis methods: IR and NMR spectroscopy, mass spectrometry, and elemental analysis. Molecular docking revealed promising compounds having an effect on influenza virus targets. The ligands have the highest calculated affinity for the “active” center of hemagglutinin, endonuclease, and PB2 protein of the RNA-dependent RNA polymerase.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2316 - 2325"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267587","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}
D. D. Chirkov, I. I. Butorin, O. S. Eltsov, P. A. Slepukhin, V. L. Rusinov
{"title":"Regioselective synthesis and oxidation of a new series of 6-nitro-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidines","authors":"D. D. Chirkov, I. I. Butorin, O. S. Eltsov, P. A. Slepukhin, V. L. Rusinov","doi":"10.1007/s11172-024-4360-1","DOIUrl":"10.1007/s11172-024-4360-1","url":null,"abstract":"<div><p>A method was developed for the synthesis of compounds of a new series of 5,7-diaryl-6-nitro-4,5,6,7-tetrahydroazolo[1,5-<i>a</i>]pyrimidines under the conditions of the Michael reaction between the corresponding triazole-containing Schiff bases and β-nitrostyrene derivative followed by additional heterocyclization. The oxidation of the resulting tetrahydro derivatives with manganese(<span>iv</span>) oxide made it possible to prepare previously unknown functional derivatives of 2-substituted 5,7-bis(4-methoxyphenyl)-6-nitro-1,2,4-triazolo-[1,5-<i>a</i>]pyrimidines, whose structures were determined using NMR correlation spectroscopy (<sup>1</sup>H—<sup>1</sup>H NOESY, <sup>1</sup>H—<sup>13</sup>C HMBC).</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2370 - 2384"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267589","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}
D. K. Trukhinov, E. A. Lebedeva, E. A. Ivanova, A. V. Lebedev, S. A. Astaf’eva
{"title":"Modification of carbon fiber with barium hexaferrite nanostructures","authors":"D. K. Trukhinov, E. A. Lebedeva, E. A. Ivanova, A. V. Lebedev, S. A. Astaf’eva","doi":"10.1007/s11172-024-4339-y","DOIUrl":"10.1007/s11172-024-4339-y","url":null,"abstract":"<div><p>A method for the preparation of a hybrid material by modifying the surface of carbon fiber with barium hexaferrite particles using ultrasonic treatment was proposed. Scanning electron microscopy, Raman spectroscopy, and X-ray diffraction were used to identify the barium hexaferrite and to reveal the structural specific features, degree of ordering and homogeneity of the carbon fibers modified with barium hexaferrite. A vibrating magnetometer was used to determine the specific magnetic moment of the obtained hybrid, which was found to be equal to ∼2.03 A m<sup>2</sup> kg<sup>−1</sup>.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 8","pages":"2184 - 2190"},"PeriodicalIF":1.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142267626","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}