M. V. Grishchenko, O. G. Khudina, G. F. Makhaeva, Ya. V. Burgart, N. V. Kovaleva, E. V. Rudakova, N. P. Boltneva, M. V. Ulitko, V. I. Saloutin, V. N. Charushin
{"title":"Conjugates of anticholinesterase drugs ipidacrine and tacrine with thiouracils: synthesis and biological properties","authors":"M. V. Grishchenko, O. G. Khudina, G. F. Makhaeva, Ya. V. Burgart, N. V. Kovaleva, E. V. Rudakova, N. P. Boltneva, M. V. Ulitko, V. I. Saloutin, V. N. Charushin","doi":"10.1007/s11172-024-4457-6","DOIUrl":"10.1007/s11172-024-4457-6","url":null,"abstract":"<div><p>Chloroalkylene amide derivatives were obtained by acylation of known Cholinesterase inhibitors, ipidacrine and tacrine. The acylated derivatives were used in the alkylation of substituted 2-thiouracils (R = Me, CF<sub>2</sub>H, CF<sub>3</sub>, (CF<sub>2</sub>)<sub>2</sub>H)) for the synthesis of new hybrid compounds. Study of the esterase profile revealed a pronounced activity and selectivity of the obtained conjugates against butyrylcholinesterase (IC<sub>50</sub> up to 2.03 µmol L<sup>−1</sup>), moderate displacement of propidium from the acetylcholinesterase peripheral anionic site, and moderate inhibition of the β-amyloid self-aggregation. It was found that conjugation of thiouracils with tacrine leads to a decrease in the hepatotoxicity of the hybrid compounds compared to that of tacrine, while in the case of ipidacrine derivatives, no hepatotoxicity was observed.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3399 - 3409"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976463","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}
V. Yu. Ivanova, V. V. Chevela, M. S. Shashin, V. E. Semenov, R. R. Zainulin
{"title":"Interaction of Xymedon with l-ascorbic acid in an aqueous solution","authors":"V. Yu. Ivanova, V. V. Chevela, M. S. Shashin, V. E. Semenov, R. R. Zainulin","doi":"10.1007/s11172-024-4455-8","DOIUrl":"10.1007/s11172-024-4455-8","url":null,"abstract":"<div><p>The interaction of Xymedon (1,2-dihydro-1-(2-hydroxyethyl)-2-oxo-4,6-dimethyl-pyrimidine, <b>1</b>) and <span>l</span>-ascorbic acid (<b>2</b>) in an aqueous solution was studied by the methods of potentiometric titration, spectroscopy in the UV—visible range, and mathematical simulation of equilibria (CPESSP program). The formation of a <b>1…2</b> associate was shown to take place at a wide change in the <i>C</i><sub>2</sub>: C<sub>1</sub> molar ratio, and its acidity constant was determined: p<i>K</i><sub>a,111</sub> = 4.95.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3381 - 3388"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976465","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}
S. L. Deev, E. S. Sheina, T. S. Shestakova, V. N. Charushin, O. N. Chupakhin
{"title":"15N-Labeled tetrazoloazines in investigation of the azido-tetrazole equilibrium","authors":"S. L. Deev, E. S. Sheina, T. S. Shestakova, V. N. Charushin, O. N. Chupakhin","doi":"10.1007/s11172-024-4431-3","DOIUrl":"10.1007/s11172-024-4431-3","url":null,"abstract":"<div><p>The data on studying the azido-tetrazole equilibrium in the tetrazoloazine series by using <sup>15</sup>N-labeled samples are reviewed. The incorporation of the <sup>15</sup>N atom significantly expands capabilities of NMR spectroscopy. An analysis of chemical shifts and <sup>1</sup>H—<sup>15</sup>N, <sup>13</sup>C—<sup>15</sup>N, and <sup>15</sup>N—<sup>15</sup>N spin-spin coupling constants is an efficient method for studying these transformations.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3113 - 3133"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976407","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}
B. S. Kuleshov, E. Yu. Poymanova, M. S. Skorotetcky, O. V. Borshchev, G. V. Cherkaev, E. V. Agina, S. A. Ponomarenko
{"title":"Crown ether-containing derivative of [1]benzothieno[3,2-b]benzothiophene for receptor layers of electrolyte-gated organic field-effect transistors","authors":"B. S. Kuleshov, E. Yu. Poymanova, M. S. Skorotetcky, O. V. Borshchev, G. V. Cherkaev, E. V. Agina, S. A. Ponomarenko","doi":"10.1007/s11172-024-4439-8","DOIUrl":"10.1007/s11172-024-4439-8","url":null,"abstract":"<div><p>We have demonstrated that electrolyte-gated organic field-effect transistors (EGOFETs) with the semiconductor layer based on [1]benzothieno[3,2-<i>b</i>]benzothiophene and the receptor layer containing 4,13-diaza-18-crown-6 ether can be used as sensors for sodium or potassium ions in solution. The proposed method for fabrication of the receptor layer allows developing a universal platform for the detection of various metal ions using crown ether structures. The EGOFETs with the receptor layer described in this work can operate in electrolyte solutions of high ionic strength, thus providing the possibility to detect sodium and potassium ions in real biological fluid samples.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3239 - 3251"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976426","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":"Study of the iodine-promoted cyclization of 4,5-diethynyl-1,2,3-triazoles for the synthesis of triazole-iodoheterocyclic dyads","authors":"A. I. Govdi, K. V. Kimele, I. A. Balova","doi":"10.1007/s11172-024-4447-8","DOIUrl":"10.1007/s11172-024-4447-8","url":null,"abstract":"<div><p>A series of functionalized 4,5-bis(arylethynyl)triazoles were prepared by a copper-catalyzed cycloaddition of 1-iodobuta-1,3-diynes and azides and subsequent Sonogashira reaction of iodoethynyltriazoles with substituted arylacetylenes. The iodine-promoted cyclization of 4,5-bis(arylethynyl)triazoles involved only one triple bond and led to the formation of 2-triazolyl-3-iodoheteroindenes or 5-(4-iodoisochromeno)triazoles.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3318 - 3323"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976432","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":"Benzoylation of Gly-Leu and Ala-Val dipeptides in aqueous—organic solvents","authors":"T. P. Kustova, L. B. Kochetova","doi":"10.1007/s11172-024-4449-6","DOIUrl":"10.1007/s11172-024-4449-6","url":null,"abstract":"<div><p>Rate constants of the reactions of Gly-<span>l</span>-Leu and <span>d</span>,<span>l</span>-Ala-<span>d</span>,<span>l</span>-Val with 2,4-dinitro- and 2,4,6-trinitrophenyl benzoates in a water—1,4-dioxane solvent under polythermal conditions were determined on the basis of the experimental study of the reaction kinetics. The rate constants vary in a range 0.5–28 L mol<sup>−1</sup> s<sup>−1</sup>. The determined activation parameters of dipeptide benzoylation are comparable with the characteristics of the related reactions within the estimation error. A significant decrease in the rate constants of dipeptide benzoylation compared with the reactions of the corresponding <i>α</i>-amino acids was found, indicating a substantial influence of the basicity of the amino compounds on their reactivity. A conclusion about the bimolecular concerted nucleophilic substitution at the carbonyl center with the nucleophile attack angle changing during the reaction was drawn on the basis of the quantum chemical calculations of the potential energy surface of the model reaction of glycyl-α-leucine with phenyl acetate in the gas phase. According to the virtual screening of the dipeptide benzoylation products, their ability to inhibit a number of hydrolase enzymes decreases noticeably compared to the dipeptides themselves, and a probability of the appearance of toxic properties decreases by 1.5–2 times. Therefore, the benzoyl derivatives of glycylleucine and alanylvaline can be considered as promising drugs.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3335 - 3341"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976434","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 bis(2,2,2-trifluoroethyl) phosphonates based on tris(2,2,2-trifluoroethyl) phosphite","authors":"Yu. N. Bubnov, A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, S. V. Baranin","doi":"10.1007/s11172-024-4459-4","DOIUrl":"10.1007/s11172-024-4459-4","url":null,"abstract":"<div><p>Convenient synthesis of functionalized bis(2,2,2-trifluoroethyl) phosphonates based on tris(2,2,2-trifluoroethyl) phosphite using <i>N</i>-chloromethylamino carboxylic acids and carbonyl compounds has been developed. The resulting compounds containing functionalized <i>N</i>-amidomethyl and phosphoryl moieties have potential biological activity, and are of interest as effective extractants and polydentate chelating ligands, as well as components of lithium-ion battery electrolytes.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3422 - 3428"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976396","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. Savinova, O. A. Kazantsev, E. A. Lapteva, S. A. Ozhogin, D. V. Orekhov, I. R. Arifullin, D. M. Kamorin, E. B. Spitsina
{"title":"Influence of amphiphilic properties of fluorophores and dyes on their interaction with molecular brushes based on oligo(ethylene glycol) methacrylates in aqueous solutions","authors":"M. V. Savinova, O. A. Kazantsev, E. A. Lapteva, S. A. Ozhogin, D. V. Orekhov, I. R. Arifullin, D. M. Kamorin, E. B. Spitsina","doi":"10.1007/s11172-024-4462-9","DOIUrl":"10.1007/s11172-024-4462-9","url":null,"abstract":"<div><p>The influence of the amphiphilic properties of of fluorophores and dyes (pyrene, methyl red, and diphenylcarbazone) on their involvement in hydrophobic cores of micelles of molecular brushes based on methoxy(oligoethylene glycol) methacrylates in aqueous solutions was determined. The polymer brushes were found to exhibit the highest sorption capacity (30–80 mg g<sup>−1</sup>) with respect to amphiphilic nonionic dye diphenylcarbazone, the lowest sorption capacity (no more than 14 mg g<sup>−1</sup>) is observed with respect to the amphiphilic ionic dye methyl red, and the sorption capacity of hydrophobic pyrene is intermediate.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3450 - 3459"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976424","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}
Z. N. Gafurov, I. K. Mikhailov, A. A. Kagilev, I. F. Sakhapov, A. O. Kantyukov, V. I. Morozov, D. A. Kulikov, E. M. Zueva, A. B. Dobrynin, A. A. Trifonov, D. G. Yakhvarov
{"title":"Electrochemical behavior of a nickel(ii) complex with an N-heterocyclic carbene bisphenolate pincer ligand","authors":"Z. N. Gafurov, I. K. Mikhailov, A. A. Kagilev, I. F. Sakhapov, A. O. Kantyukov, V. I. Morozov, D. A. Kulikov, E. M. Zueva, A. B. Dobrynin, A. A. Trifonov, D. G. Yakhvarov","doi":"10.1007/s11172-024-4441-1","DOIUrl":"10.1007/s11172-024-4441-1","url":null,"abstract":"<div><p>The electrochemical behavior of the N-heterocyclic carbene bisphenolate complex of nickel(<span>ii</span>) Ni(L)Py (L – 1,3-bis(3,5-di-<i>tert</i>-butyl-2-phenolato)-5,5-dimethyl-(4,6-dihydropyrimidin-2-ylidene)) was studied using cyclic voltammetry and EPR spectroelectrochemistry. According to the obtained experimental data supplemented by quantum chemical calculations, the electrochemical properties of this complex differ significantly from those of its benzimidazolylidene and imidazolylidene analogs. The oxidation of the Ni(L)Py complex is a ligand-centered process, and the phenoxyl radical group formed is susceptible to decoordination and interaction with the NHC-fragment of the complex to form benzoxazole, the crystal structure of which was determined by X-ray diffraction.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3259 - 3266"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976357","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. G. Mirochnik, E. V. Fedorenko, A. V. Gerasimenko, D. Kh. Shlyk, A. Yu. Beloliptsev, A. B. Podgorbunsky, A. M. Ziatdinov
{"title":"Semiconductor and luminescent properties of boron difluoride curcuminoid crystals","authors":"A. G. Mirochnik, E. V. Fedorenko, A. V. Gerasimenko, D. Kh. Shlyk, A. Yu. Beloliptsev, A. B. Podgorbunsky, A. M. Ziatdinov","doi":"10.1007/s11172-024-4443-z","DOIUrl":"10.1007/s11172-024-4443-z","url":null,"abstract":"<div><p>The electrical conductive, paramagnetic, and luminescent properties of boron coordination compounds based on boron difluoride curcuminoid (1-[4′-(dimethylamino)-phenyl]-4-phenyl-but-1-ene-2,4-dionate) (<b>1</b>) were investigated. The single-crystal X-ray diffraction study of compound <b>1</b> was performed. The electrical conductivity of complex <b>1</b> in the crystalline state (∼10<sup>−4</sup> S cm<sup>−1</sup>) is similar to the values characteristic of electrically conductive polymers from a number of aromatic amines. The UV irradiation of the crystals of <b>1</b> induces the formation of metastable paramagnetic centers, which have a lifetime lasting for hours at low temperatures. The luminescence spectrum of the crystals of <b>1</b> at <i>λ</i><sub>ex</sub> = 370 nm shows two bands in the blue and near-IR regions (470 and 800 nm, respectively). The discovered semiconductor, luminescent, and paramagnetic properties of the crystals of <b>1</b> may be useful in the development of smart materials for optoelectronics.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 11","pages":"3275 - 3284"},"PeriodicalIF":1.7,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976361","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}