This review generalizes diverse computational NMR studies of different natural products involving true alkaloids (indole, quinolizidine, pyrrolizidine, piperidine, indolizidine, quinoline, isoquinoline, indoloquinoline, and guanidine alkaloids), pseudoalkaloids (terpenes and steroids), quinones, lactones, lactams, flavonoids, and many others. The diverse computational protocols employed in each particular case are thoroughly discussed with a special emphasis on their structural and stereochemical applications. The bibliography includes 165 references.
{"title":"Computational NMR of natural products","authors":"V. Semenov, L. Krivdin","doi":"10.1070/RCR5027","DOIUrl":"https://doi.org/10.1070/RCR5027","url":null,"abstract":"This review generalizes diverse computational NMR studies of different natural products involving true alkaloids (indole, quinolizidine, pyrrolizidine, piperidine, indolizidine, quinoline, isoquinoline, indoloquinoline, and guanidine alkaloids), pseudoalkaloids (terpenes and steroids), quinones, lactones, lactams, flavonoids, and many others. The diverse computational protocols employed in each particular case are thoroughly discussed with a special emphasis on their structural and stereochemical applications. The bibliography includes 165 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"91 1","pages":""},"PeriodicalIF":7.7,"publicationDate":"2021-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43667258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. Valeeva, A. Rempel, S. Rempel, S. Sadovnikov, A. Gusev
The results of recent experimental studies of the influence of the size of oxide, carbide and sulfide nanoparticles on changes in their nonstoichiometry are analyzed and generalized. In relation to intrinsically nonstoichiometric titanium oxides and niobium and vanadium carbides, on the one hand, and stoichiometric silver sulfides, on the other hand, it is shown that a decrease in the particle size to the nano scale has a strong impact on the chemical composition of nanocrystalline compounds, viz., it leads to the occurrence of or increase in nonstoichiometry. A conclusion is drawn that interplay between the particle size and nonstoichiometry is common to all solid nanocrystalline substances and should be taken into account in studies on the synthesis, structure and properties of these systems. The bibliography includes 260 references.
{"title":"Nonstoichiometry, structure and properties of nanocrystalline oxides, carbides and sulfides","authors":"A. Valeeva, A. Rempel, S. Rempel, S. Sadovnikov, A. Gusev","doi":"10.1070/RCR4967","DOIUrl":"https://doi.org/10.1070/RCR4967","url":null,"abstract":"The results of recent experimental studies of the influence of the size of oxide, carbide and sulfide nanoparticles on changes in their nonstoichiometry are analyzed and generalized. In relation to intrinsically nonstoichiometric titanium oxides and niobium and vanadium carbides, on the one hand, and stoichiometric silver sulfides, on the other hand, it is shown that a decrease in the particle size to the nano scale has a strong impact on the chemical composition of nanocrystalline compounds, viz., it leads to the occurrence of or increase in nonstoichiometry. A conclusion is drawn that interplay between the particle size and nonstoichiometry is common to all solid nanocrystalline substances and should be taken into account in studies on the synthesis, structure and properties of these systems. The bibliography includes 260 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"601 - 626"},"PeriodicalIF":7.7,"publicationDate":"2021-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47259697","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The review presents data on the synthesis, structure, reactivity, and catalytic activity of alkyl derivatives of rare earth metals in the oxidation state +2 (Sm, Eu, Yb) and their analogues containing heavy alkaline earth metals (Ca, Sr, Ba). The synthetic aspects and structural features of this unique class of organometallic compounds, which contain highly reactive M–C bonds, including alkyl, α-silylmethyl, and also benzyl, diphenylmethyl, and triphenylmethyl derivatives are considered. The bibliography includes 157 references.
{"title":"Alkyl complexes of divalent lanthanides and heavy alkaline earth metals","authors":"D. Khristolyubov, D. Lyubov, A. Trifonov","doi":"10.1070/RCR4992","DOIUrl":"https://doi.org/10.1070/RCR4992","url":null,"abstract":"The review presents data on the synthesis, structure, reactivity, and catalytic activity of alkyl derivatives of rare earth metals in the oxidation state +2 (Sm, Eu, Yb) and their analogues containing heavy alkaline earth metals (Ca, Sr, Ba). The synthetic aspects and structural features of this unique class of organometallic compounds, which contain highly reactive M–C bonds, including alkyl, α-silylmethyl, and also benzyl, diphenylmethyl, and triphenylmethyl derivatives are considered. The bibliography includes 157 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"529 - 565"},"PeriodicalIF":7.7,"publicationDate":"2021-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47936790","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The review aims to draw attention to the latest advances in the organoboron chemistry and therapeutic use of organoboron compounds. The synthetic strategies towards boron-containing compounds with proven in vitro and/or in vivo biological activities, including derivatives of boronic acids, benzoxaboroles, benzoxaborines and benzodiazaborines, are summarized. Approaches to the synthesis of hybrid structures containing an organoboron moiety as one of the pharmacophores are considered, and the effect of this modification on the pharmacological activity of the initial molecules is analyzed. On the basis of analysis of the published data, the most promising areas of research in the field of organoboron compounds are identified, including the latest methods of synthesis, modification and design of effective therapeutic agents. The bibliography includes 246 references.
{"title":"Progress in the medicinal chemistry of organoboron compounds","authors":"A. Tevyashova, M. Chudinov","doi":"10.1070/RCR4977","DOIUrl":"https://doi.org/10.1070/RCR4977","url":null,"abstract":"The review aims to draw attention to the latest advances in the organoboron chemistry and therapeutic use of organoboron compounds. The synthetic strategies towards boron-containing compounds with proven in vitro and/or in vivo biological activities, including derivatives of boronic acids, benzoxaboroles, benzoxaborines and benzodiazaborines, are summarized. Approaches to the synthesis of hybrid structures containing an organoboron moiety as one of the pharmacophores are considered, and the effect of this modification on the pharmacological activity of the initial molecules is analyzed. On the basis of analysis of the published data, the most promising areas of research in the field of organoboron compounds are identified, including the latest methods of synthesis, modification and design of effective therapeutic agents. The bibliography includes 246 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"451 - 487"},"PeriodicalIF":7.7,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44803223","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The revies focuses on low-molecular-weight plant metabolites (mono- and sesquiterpenes) exhibiting antiviral activity. Data on antiviral action of both essential oils and plant extracts and their components are provided. Structures of biologically active natural mono- and sesquiterpenoids as well as their derivatives showing a pronounced antiviral activity are presented. A special attention is given to the description of targets for antiviral therapy. The mechanisms of action of antiviral agents are considered. The bibliography includes 163 references.
{"title":"Mono- and sesquiterpenes as a starting platform for the development of antiviral drugs","authors":"O. Yarovaya, N. Salakhutdinov","doi":"10.1070/RCR4969","DOIUrl":"https://doi.org/10.1070/RCR4969","url":null,"abstract":"The revies focuses on low-molecular-weight plant metabolites (mono- and sesquiterpenes) exhibiting antiviral activity. Data on antiviral action of both essential oils and plant extracts and their components are provided. Structures of biologically active natural mono- and sesquiterpenoids as well as their derivatives showing a pronounced antiviral activity are presented. A special attention is given to the description of targets for antiviral therapy. The mechanisms of action of antiviral agents are considered. The bibliography includes 163 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"488 - 510"},"PeriodicalIF":7.7,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47994479","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The review summarizes and systematizes the [4+2]-cycloaddition reactions of o-quinone methides with electron-rich and electron-deficient olefins. The electron-rich substrates include vinyl ethers, vinyl sulfides, enamines, enamides, enols, furans, benzofurans and indoles, while the electron-deficient substrates are esters of unsaturated carboxylic acids, vinyl azides and quinones. Reactions with push-pull and captodative olefins are also considered. The mechanisms of some reactions are presented. A separate part of the review addresses reactions of p-quinone methides containing an o-hydroxyphenyl substituent at the exocyclic carbon atom, which can isomerize to o-quinone methides. Much attention is paid to oligomerization of o-quinone methides, which proceeds in the absence of active dienophiles or nucleophiles. The bibliography includes 217 references.
{"title":"Cycloaddition reactions of o-quinone methides with polarized olefins","authors":"V. Osyanin, A. V. Lukashenko, D. Osipov","doi":"10.1070/RCR4971","DOIUrl":"https://doi.org/10.1070/RCR4971","url":null,"abstract":"The review summarizes and systematizes the [4+2]-cycloaddition reactions of o-quinone methides with electron-rich and electron-deficient olefins. The electron-rich substrates include vinyl ethers, vinyl sulfides, enamines, enamides, enols, furans, benzofurans and indoles, while the electron-deficient substrates are esters of unsaturated carboxylic acids, vinyl azides and quinones. Reactions with push-pull and captodative olefins are also considered. The mechanisms of some reactions are presented. A separate part of the review addresses reactions of p-quinone methides containing an o-hydroxyphenyl substituent at the exocyclic carbon atom, which can isomerize to o-quinone methides. Much attention is paid to oligomerization of o-quinone methides, which proceeds in the absence of active dienophiles or nucleophiles. The bibliography includes 217 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"324 - 373"},"PeriodicalIF":7.7,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42199831","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
For the first time, the literature data on the methods of synthesis and reactivity of 3-(1-alkynyl)chromones are summarized and systematized. The main method for obtaining these compounds is the Sonogashira cross-coupling reaction of 3-halochromones with terminal acetylenes, and their most important chemical properties include the transformation into furans, reactions with dinucleophiles, ambiphilic [4+2]- and [4+3]-cyclizations, and also dimerization and mixed condensation of 2-methyl-3-(1-alkynyl)chromones due to the vinylogous methyl group. Except for the oxacyclization to furans, chemical transformations of 3-(1-alkynyl)chromones are accompanied by pyrone ring transformation, in which not only the carbonyl group but also the triple bond can participate. This significantly increases the synthetic value of these compounds and ensures the production of more complex heterocyclic systems based on them. The mechanisms of the reactions are discussed, the conditions for their implementation and the yields of the resulting products are indicated. The bibliography includes 80 references.
{"title":"Synthesis and reactivity of 3-(1-alkynyl)chromones","authors":"V. Sosnovskikh","doi":"10.1070/RCR5008","DOIUrl":"https://doi.org/10.1070/RCR5008","url":null,"abstract":"For the first time, the literature data on the methods of synthesis and reactivity of 3-(1-alkynyl)chromones are summarized and systematized. The main method for obtaining these compounds is the Sonogashira cross-coupling reaction of 3-halochromones with terminal acetylenes, and their most important chemical properties include the transformation into furans, reactions with dinucleophiles, ambiphilic [4+2]- and [4+3]-cyclizations, and also dimerization and mixed condensation of 2-methyl-3-(1-alkynyl)chromones due to the vinylogous methyl group. Except for the oxacyclization to furans, chemical transformations of 3-(1-alkynyl)chromones are accompanied by pyrone ring transformation, in which not only the carbonyl group but also the triple bond can participate. This significantly increases the synthetic value of these compounds and ensures the production of more complex heterocyclic systems based on them. The mechanisms of the reactions are discussed, the conditions for their implementation and the yields of the resulting products are indicated. The bibliography includes 80 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"511 - 527"},"PeriodicalIF":7.7,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49320018","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. Masoud, D. Vorobyeva, Dmitry A. Petropavlovskikh, C. Bruneau, S. Osipov
The review summarizes literature data on the methods for the introduction of fluorine atoms and fluoralkyl groups into different ligands to construct metathesis-active ruthenium carbene complexes. It also analyzes the influence of fluorinated ligands on the catalytic activity of the complexes. The choice, structure and positions of fluorinated substituents in NHC ligands are generally dictated by the desire to increase the electrophilicity of the ruthenium atom due to the electron-withdrawing effect of fluorine atoms and fluoroalkyl groups, resulting, as a rule, in an increase in the activity of the ruthenium complex. In catalysts with unsymmetrical fluorine-containing NHC ligands, there is a possibility of additional Ru–F coordination, making the complexes much more stable and, consequently, more active. The presence of fluorine in chelating alkylidene ligands provides an increase in the catalyst initiation rate due to a weakening of the ruthenium – heteroatom bond. Besides, the introduction of polyfluoroalkyl groups into ligands solves the problem of catalyst recovery using fluorous biphasic systems for reuse. The bibliography includes 172 references.
{"title":"Fluorine-containing ruthenium-based olefin metathesis catalysts","authors":"S. Masoud, D. Vorobyeva, Dmitry A. Petropavlovskikh, C. Bruneau, S. Osipov","doi":"10.1070/RCR4984","DOIUrl":"https://doi.org/10.1070/RCR4984","url":null,"abstract":"The review summarizes literature data on the methods for the introduction of fluorine atoms and fluoralkyl groups into different ligands to construct metathesis-active ruthenium carbene complexes. It also analyzes the influence of fluorinated ligands on the catalytic activity of the complexes. The choice, structure and positions of fluorinated substituents in NHC ligands are generally dictated by the desire to increase the electrophilicity of the ruthenium atom due to the electron-withdrawing effect of fluorine atoms and fluoroalkyl groups, resulting, as a rule, in an increase in the activity of the ruthenium complex. In catalysts with unsymmetrical fluorine-containing NHC ligands, there is a possibility of additional Ru–F coordination, making the complexes much more stable and, consequently, more active. The presence of fluorine in chelating alkylidene ligands provides an increase in the catalyst initiation rate due to a weakening of the ruthenium – heteroatom bond. Besides, the introduction of polyfluoroalkyl groups into ligands solves the problem of catalyst recovery using fluorous biphasic systems for reuse. The bibliography includes 172 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"419 - 450"},"PeriodicalIF":7.7,"publicationDate":"2021-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45571665","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Characteristic features of the Ostwald ripening in oil-in-water and water-in-oil macro- and nanoemulsions are analyzed. Methods for reducing the ripening rate are considered. It is shown that Ostwald ripening is especially relevant for nanoemulsions, and this is often the main process leading to degradation of nanoemulsions, thus limiting their practical applications. Considerable attention is paid to the debatable issue of the role of surfactants in the mass transfer between the droplets of the dispersed phase. Analysis of published sources shows that if the solubility of the dispersed phase substance in the dispersion medium is not extremely low, then the major contribution to Ostwald ripening is made by molecular diffusion. If the solubility of the dispersed phase substance is very low, then micelles and nanodroplets are the most likely carriers of the substances through the dispersion medium. Nanodroplets and slightly larger droplets are formed on the surface of droplets of the starting emulsion because of the interfacial instability (Marangoni effect). The bibliography includes 204 references.
{"title":"Ostwald ripening in macro- and nanoemulsions","authors":"M. Koroleva, E. Yurtov","doi":"10.1070/RCR4962","DOIUrl":"https://doi.org/10.1070/RCR4962","url":null,"abstract":"Characteristic features of the Ostwald ripening in oil-in-water and water-in-oil macro- and nanoemulsions are analyzed. Methods for reducing the ripening rate are considered. It is shown that Ostwald ripening is especially relevant for nanoemulsions, and this is often the main process leading to degradation of nanoemulsions, thus limiting their practical applications. Considerable attention is paid to the debatable issue of the role of surfactants in the mass transfer between the droplets of the dispersed phase. Analysis of published sources shows that if the solubility of the dispersed phase substance in the dispersion medium is not extremely low, then the major contribution to Ostwald ripening is made by molecular diffusion. If the solubility of the dispersed phase substance is very low, then micelles and nanodroplets are the most likely carriers of the substances through the dispersion medium. Nanodroplets and slightly larger droplets are formed on the surface of droplets of the starting emulsion because of the interfacial instability (Marangoni effect). The bibliography includes 204 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"90 1","pages":"293 - 323"},"PeriodicalIF":7.7,"publicationDate":"2021-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45890244","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The preservation of DNA has attracted significant interest of scientists in diverse research fields from ancient biological remains to the information field. In light of the different DNA safekeeping requirements (e.g., storage time, storage conditions) in these disparate fields, scientists have proposed distinct methods to maintain the DNA integrity. Specifically, DNA data storage is an emerging research, which means that the binary digital information is converted to the sequences of nucleotides leading to dense and durable data storage in the form of synthesized DNA. The intact preservation of DNA plays a significant role because it is closely related to data integrity. This review discusses DNA preservation methods, aiming to confirm an appropriate one for synthetic oligonucleotides in DNA data storage. First, we analyze the impact factors of the DNA long-term storage, including the intrinsic stability of DNA, environmental factors, and storage methods. Then, the benefits and disadvantages of diverse conservation approaches (e.g., encapsulation-free, chemical encapsulation) are discussed. Finally, we provide advice for storing non-genetic information in DNA in vitro. We expect these preservation suggestions to promote further research that may extend the DNA storage time. The bibliography includes 99 references.
{"title":"Preservation of DNA for data storage","authors":"Xin Tan, L. Ge, Tianzhu Zhang, Zuhong Lu","doi":"10.1070/RCR4994","DOIUrl":"https://doi.org/10.1070/RCR4994","url":null,"abstract":"The preservation of DNA has attracted significant interest of scientists in diverse research fields from ancient biological remains to the information field. In light of the different DNA safekeeping requirements (e.g., storage time, storage conditions) in these disparate fields, scientists have proposed distinct methods to maintain the DNA integrity. Specifically, DNA data storage is an emerging research, which means that the binary digital information is converted to the sequences of nucleotides leading to dense and durable data storage in the form of synthesized DNA. The intact preservation of DNA plays a significant role because it is closely related to data integrity. This review discusses DNA preservation methods, aiming to confirm an appropriate one for synthetic oligonucleotides in DNA data storage. First, we analyze the impact factors of the DNA long-term storage, including the intrinsic stability of DNA, environmental factors, and storage methods. Then, the benefits and disadvantages of diverse conservation approaches (e.g., encapsulation-free, chemical encapsulation) are discussed. Finally, we provide advice for storing non-genetic information in DNA in vitro. We expect these preservation suggestions to promote further research that may extend the DNA storage time. The bibliography includes 99 references.","PeriodicalId":21523,"journal":{"name":"Russian Chemical Reviews","volume":"1 1","pages":"280 - 291"},"PeriodicalIF":7.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"59009434","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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