Irina Balova | Saint-Petersburg State University (original) (raw)
Papers by Irina Balova
Organic & biomolecular chemistry, 2024
Journal of the Chemical Society, 2002
ABSTRACT
Russian Journal of General Chemistry, Aug 1, 2008
Organometallics, Jul 15, 2003
ABSTRACT Reactions of [H2Os3(CO)10] with a series of diynes, RC2C2R‘ (1: R = Ph, R‘ = CH2OH; 2: R... more ABSTRACT Reactions of [H2Os3(CO)10] with a series of diynes, RC2C2R‘ (1: R = Ph, R‘ = CH2OH; 2: R = Ph, R‘ = C(O)Ph; 3: R = R‘ = C(OH)Me2), have been studied. It was found that upon coordination to the triosmium cluster, the nucleophilic oxygens of the R‘ substituents of 1 and 2 take part in intramolecular cyclization reactions to give [HOs3(CO)10{μ-η1:η2-PhCH2(CCH−CCH−O)}] (5) and [HOs3(CO)10{μ-η1:η1-Ph(CCH−CC−O)CPh}] (6), respectively, both of which contain furan rings coordinated to the cluster core. On heating of the latter compound, the furan moiety remains intact, but a carbonyl group dissociates from the cluster, leading to the formation of [HOs3(CO)9(μ3-η1:η3:η1-Ph(CCH−CC−O)CPh)] (7) with a closed “C3Os3” pentagonal pyramidal structure. Reaction of [H2Os3(CO)10] with 3 does not lead to cyclization of the diyne; instead, the clusters [Os3(CO)10{μ3-η2-(RCHCH−C2R)}] (8) and [Os3(CO)10{μ3-η2-(RC2C2R)}] (9) are formed. Deuterium labeling of the starting compounds has been used in the reaction of [H2Os3(CO)10] with HOCH2C2C2CH2OH in order to investigate possible mechanisms of the cyclization reaction. The crystal and molecular structures of clusters 5, 7, and 9 are presented.
International Journal of Molecular Sciences, Feb 24, 2023
ChemInform, Jul 25, 2013
Catalytic Activity of Palladium(II) Diaminocarbene Complexes in the Sonogashira and Suzuki Reacti... more Catalytic Activity of Palladium(II) Diaminocarbene Complexes in the Sonogashira and Suzuki Reactions.-Cross-coupling reactions of haloarenes with oct-1-yne (Sonogashira reaction) and phenylboronic acid (Suzuki reaction) are presented using palladium(II) complexes with chelating and non-chelating diaminocarbene ligands as catalysts. Both catalysts show higher activity than traditional phosphine ligand based systems in the Sonogashira reaction.-(MIKHAILOV, V. N.;
Chemistry – A European Journal
Fluorescent isocoumarin‐fused cycloalkynes, which are reactive in SPAAC and give fluorescent tria... more Fluorescent isocoumarin‐fused cycloalkynes, which are reactive in SPAAC and give fluorescent triazoles regardless of the azide nature, have been developed. The key structural feature that converts the non‐fluorescent cycloalkyne/triazole pair to its fluorescent counterpart is the pi‐acceptor group (COOMe, CN) at the C6 position of the isocoumarin ring. The design of the fluorescent cycloalkyne/triazole pairs is based on the theoretical study of the S1 state deactivation mechanism of the non‐fluorescent isocoumarin‐fused cycloalkyne IC9O using multi‐configurational ab initio and DFT methodologies. The calculations revealed that deactivation proceeds through the electrocyclic ring opening of the α‐pyrone cycle and is accompanied by a redistribution of electron density in the fused benzene ring. We proposed that the S1 excited state deactivation barrier could be increased by introducing a pi‐acceptor group into a position that is in direct conjugation with the formed C=O group and has ...
Russian Chemical Bulletin
International Journal of Molecular Sciences
Dual inhibitors of protein phosphotyrosine phosphatase 1B (PTP1B)/T-cell protein phosphotyrosine ... more Dual inhibitors of protein phosphotyrosine phosphatase 1B (PTP1B)/T-cell protein phosphotyrosine phosphatase (TC-PTP) based on the 3-(hydroxymethyl)-4-oxo-1,4-dihydrocinnoline scaffold have been identified. Their dual affinity to both enzymes has been thoroughly corroborated by in silico modeling experiments. The compounds have been profiled in vivo for their effects on body weight and food intake in obese rats. Likewise, the effects of the compounds on glucose tolerance, insulin resistance, as well as insulin and leptin levels, have been evaluated. In addition, the effects on PTP1B, TC-PTP, and Src homology region 2 domain-containing phosphatase-1 (SHP1), as well as the insulin and leptin receptors gene expressions, have been assessed. In obese male Wistar rats, a five-day administration of all studied compounds led to a decrease in body weight and food intake, improved glucose tolerance, attenuated hyperinsulinemia, hyperleptinemia and insulin resistance, and also compensatory inc...
Chemistry of Heterocyclic Compounds
Russian Journal of General Chemistry
The carbene transfer from N-heterocyclic carbene complexes of Group 11 metals (NHC–MC) (especiall... more The carbene transfer from N-heterocyclic carbene complexes of Group 11 metals (NHC–MC) (especially silver and copper) to other metals is considered a convenient and universal, sometimes having no alternative, method for the synthesis of a wide range of important N-heterocyclic carbene complexes of transition metals. As the number of successful examples of transmetalation with the formation of the target product has increased, the data were accumulated on alternative or unexpected results of the interaction of NHC–MC complexes with compounds of other metals. This review considers the examples of NHC–MC reactions with compounds of other metals which proceed with a change in the metals oxidation state, conversion of (NHC)MCX into cationic homoleptic [(NHC)2MC]+ forms, transmetalation retaining the other metal in the coordination sphere of the product, or formation of heterometallic adducts preserving the MC–Ccarbene bond, rather than these occurring according to the standard reaction pathway. Unusual “reverse” carbene transfer reactions have been considered separately. The review material reveals a promising new synthetic potential of NHC–MC in the reactions with other metals and discusses the possible mechanisms and driving forces of such transformations. The most important aspects of the application of the obtained products, primarily in various catalytic processes, have been considered as well.
Molecules
Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequ... more Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push–pull chromophores: 4,5-bis(arylethynyl)-1H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles’ application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.
SSRN Electronic Journal, 2022
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Dalton Transactions, 2021
Air-stable copper(i) N-heterocyclic carbene complexes are excellent reagents for carbene transfer... more Air-stable copper(i) N-heterocyclic carbene complexes are excellent reagents for carbene transfer to Lewis Acids based on group 13 metals.
UV-spectra of two disubstituted diacetylenes, phenyldiacetylene and nine monoand disubstituted ph... more UV-spectra of two disubstituted diacetylenes, phenyldiacetylene and nine monoand disubstituted phenyldiacetylenes have been measured in several solvents in an interval 240-400 am. Well resolved vibronic structure is revealed. There are bathochrome and hyperchrome effects on lengthening of conjugation bonds chain. Distortion of this chain linearity leads to vibronic structure smuthing.
Organic & biomolecular chemistry, 2024
Journal of the Chemical Society, 2002
ABSTRACT
Russian Journal of General Chemistry, Aug 1, 2008
Organometallics, Jul 15, 2003
ABSTRACT Reactions of [H2Os3(CO)10] with a series of diynes, RC2C2R‘ (1: R = Ph, R‘ = CH2OH; 2: R... more ABSTRACT Reactions of [H2Os3(CO)10] with a series of diynes, RC2C2R‘ (1: R = Ph, R‘ = CH2OH; 2: R = Ph, R‘ = C(O)Ph; 3: R = R‘ = C(OH)Me2), have been studied. It was found that upon coordination to the triosmium cluster, the nucleophilic oxygens of the R‘ substituents of 1 and 2 take part in intramolecular cyclization reactions to give [HOs3(CO)10{μ-η1:η2-PhCH2(CCH−CCH−O)}] (5) and [HOs3(CO)10{μ-η1:η1-Ph(CCH−CC−O)CPh}] (6), respectively, both of which contain furan rings coordinated to the cluster core. On heating of the latter compound, the furan moiety remains intact, but a carbonyl group dissociates from the cluster, leading to the formation of [HOs3(CO)9(μ3-η1:η3:η1-Ph(CCH−CC−O)CPh)] (7) with a closed “C3Os3” pentagonal pyramidal structure. Reaction of [H2Os3(CO)10] with 3 does not lead to cyclization of the diyne; instead, the clusters [Os3(CO)10{μ3-η2-(RCHCH−C2R)}] (8) and [Os3(CO)10{μ3-η2-(RC2C2R)}] (9) are formed. Deuterium labeling of the starting compounds has been used in the reaction of [H2Os3(CO)10] with HOCH2C2C2CH2OH in order to investigate possible mechanisms of the cyclization reaction. The crystal and molecular structures of clusters 5, 7, and 9 are presented.
International Journal of Molecular Sciences, Feb 24, 2023
ChemInform, Jul 25, 2013
Catalytic Activity of Palladium(II) Diaminocarbene Complexes in the Sonogashira and Suzuki Reacti... more Catalytic Activity of Palladium(II) Diaminocarbene Complexes in the Sonogashira and Suzuki Reactions.-Cross-coupling reactions of haloarenes with oct-1-yne (Sonogashira reaction) and phenylboronic acid (Suzuki reaction) are presented using palladium(II) complexes with chelating and non-chelating diaminocarbene ligands as catalysts. Both catalysts show higher activity than traditional phosphine ligand based systems in the Sonogashira reaction.-(MIKHAILOV, V. N.;
Chemistry – A European Journal
Fluorescent isocoumarin‐fused cycloalkynes, which are reactive in SPAAC and give fluorescent tria... more Fluorescent isocoumarin‐fused cycloalkynes, which are reactive in SPAAC and give fluorescent triazoles regardless of the azide nature, have been developed. The key structural feature that converts the non‐fluorescent cycloalkyne/triazole pair to its fluorescent counterpart is the pi‐acceptor group (COOMe, CN) at the C6 position of the isocoumarin ring. The design of the fluorescent cycloalkyne/triazole pairs is based on the theoretical study of the S1 state deactivation mechanism of the non‐fluorescent isocoumarin‐fused cycloalkyne IC9O using multi‐configurational ab initio and DFT methodologies. The calculations revealed that deactivation proceeds through the electrocyclic ring opening of the α‐pyrone cycle and is accompanied by a redistribution of electron density in the fused benzene ring. We proposed that the S1 excited state deactivation barrier could be increased by introducing a pi‐acceptor group into a position that is in direct conjugation with the formed C=O group and has ...
Russian Chemical Bulletin
International Journal of Molecular Sciences
Dual inhibitors of protein phosphotyrosine phosphatase 1B (PTP1B)/T-cell protein phosphotyrosine ... more Dual inhibitors of protein phosphotyrosine phosphatase 1B (PTP1B)/T-cell protein phosphotyrosine phosphatase (TC-PTP) based on the 3-(hydroxymethyl)-4-oxo-1,4-dihydrocinnoline scaffold have been identified. Their dual affinity to both enzymes has been thoroughly corroborated by in silico modeling experiments. The compounds have been profiled in vivo for their effects on body weight and food intake in obese rats. Likewise, the effects of the compounds on glucose tolerance, insulin resistance, as well as insulin and leptin levels, have been evaluated. In addition, the effects on PTP1B, TC-PTP, and Src homology region 2 domain-containing phosphatase-1 (SHP1), as well as the insulin and leptin receptors gene expressions, have been assessed. In obese male Wistar rats, a five-day administration of all studied compounds led to a decrease in body weight and food intake, improved glucose tolerance, attenuated hyperinsulinemia, hyperleptinemia and insulin resistance, and also compensatory inc...
Chemistry of Heterocyclic Compounds
Russian Journal of General Chemistry
The carbene transfer from N-heterocyclic carbene complexes of Group 11 metals (NHC–MC) (especiall... more The carbene transfer from N-heterocyclic carbene complexes of Group 11 metals (NHC–MC) (especially silver and copper) to other metals is considered a convenient and universal, sometimes having no alternative, method for the synthesis of a wide range of important N-heterocyclic carbene complexes of transition metals. As the number of successful examples of transmetalation with the formation of the target product has increased, the data were accumulated on alternative or unexpected results of the interaction of NHC–MC complexes with compounds of other metals. This review considers the examples of NHC–MC reactions with compounds of other metals which proceed with a change in the metals oxidation state, conversion of (NHC)MCX into cationic homoleptic [(NHC)2MC]+ forms, transmetalation retaining the other metal in the coordination sphere of the product, or formation of heterometallic adducts preserving the MC–Ccarbene bond, rather than these occurring according to the standard reaction pathway. Unusual “reverse” carbene transfer reactions have been considered separately. The review material reveals a promising new synthetic potential of NHC–MC in the reactions with other metals and discusses the possible mechanisms and driving forces of such transformations. The most important aspects of the application of the obtained products, primarily in various catalytic processes, have been considered as well.
Molecules
Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequ... more Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push–pull chromophores: 4,5-bis(arylethynyl)-1H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles’ application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.
SSRN Electronic Journal, 2022
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Dalton Transactions, 2021
Air-stable copper(i) N-heterocyclic carbene complexes are excellent reagents for carbene transfer... more Air-stable copper(i) N-heterocyclic carbene complexes are excellent reagents for carbene transfer to Lewis Acids based on group 13 metals.
UV-spectra of two disubstituted diacetylenes, phenyldiacetylene and nine monoand disubstituted ph... more UV-spectra of two disubstituted diacetylenes, phenyldiacetylene and nine monoand disubstituted phenyldiacetylenes have been measured in several solvents in an interval 240-400 am. Well resolved vibronic structure is revealed. There are bathochrome and hyperchrome effects on lengthening of conjugation bonds chain. Distortion of this chain linearity leads to vibronic structure smuthing.