Перегляд за Автор "Bondarenko, Svetlana"
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Документ Alkaloid-Flavonoid Conjugates(2015) Bondarenko, Svetlana; Khilya, Volodimir; Popova, Antonina; Frasinyuk, MihayloДокумент Aminomethylation of 3-aryl-7-hydroxycoumarins(2010) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, VolodimirThe reaction of the analogs of natural 3-arylbenzopyran-2-ones with electrophilic reagents of aminal structure was studied. Substituted 8-aminomethyl-3-aryl-7-hydroxycoumarins were synthesized. The optimum conditions were determined for the production of 9-alkyl- and 9-(het)arylmethyl derivatives of 3-aryl-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-2-one in the series of analogs of natural 3-arylbenzopyran-2-ones.Документ Aminomethylation of formononetin and cladrin by primary amines(2009) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, VolodimirThe reaction of natural isoflavones formononetin and cladrin with primary amines and formalin in the presence of a base catalyst was studied. Several novel substituted 9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-ones containing alkyl, benzyl, or heterylalkyl substituents in the N-9 position were synthesized.Документ Aurone Mannich bases as synthones for an inverse electron demand Diels-Alder reaction(2017) Popova, Antonina; Bondarenko, Svetlana; Frasinyuk, MihayloДокумент Chain-chain tautomerism of ω-aminoalcohol aminomethyl derivatives(2018) Danylchenko, V. Ye.; Bondarenko, Svetlana; Mrug, Galyna; Kondratyuk, K. M.; Frasinyuk, MihayloThe aminomethylation reaction of 2-naphtol, umbelliferon, and 7- hydroxyisoflavones using ω -aminoalcohols and paraformaldehyde was studied. The products of reaction exist as tautomeric mixtures which was confirmed by 2D NOESY spectra. The ratio of tautomers depends on carbon chain length of ω-aminoalcohol, solvent, and pH. The major form of 2-aminoethanol derivatives is 1,3-benzoxazine. However, low-polar solvents shift equilibrium toward 1,3-oxazoline form. Derivatives of 3-aminopropanol are preferably exist as 1,3-oxazoline form in all solvents. The mixture of tautomers also was indicated for 4-aminobutanol derivatives, but 5-aminopentanol derivatives exist only in 1,3- benzoxazine formДокумент Cytisine derivatives as new anti-Escherichia coli agents: in silico and in vitro studies(2021) Hodyna, Diana; Kovalishin, Vasyl; Blagodatnyi, Volodymyr; Bondarenko, Svetlana; Mrug, Galyna; Frasinyuk, Mihaylo; Metelytsia, LarysaQSAR analysis of a 5143 compounds set of previously synthesized compounds tested against multi-drug resistant (MDR) clinical isolate Escherichia coli strains was done by using Online Chemical Modeling Environment (OCHEM).The predictive ability of the regression models was tested through cross-validation, giving coefficient of determination q2 = 0.72-0.8. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with reasonable accuracy within the applicability domain (q2 = 0.74-0.8). The models were applied to screen a virtual chemical library of cytisine derivatives, which was designed to have antibacterial activity. The QSAR modeling results allowed to identify a number of cytisine derivatives as effective antibacterial agents against antibiotic-resistant E. coli strains. Seven compounds were selected for synthesis and biological testing. In vitro investigation of the selected cytisine derivatives have shown that all studied compounds are potential antibacterial agents against MDR E. coli strains.Документ Extracting P - vitamin complex from green tea leaves(2014) Podobiy, Olena; Bondarenko, Svetlana; Yarosh, Anastasia; Ladonko, MarinaP - vitamin complex from green tea has high antioxidant action of catechins, so it can be used to prevent and treat the most common diseases in the pathogenesis of which activation of free radical oxidation plays an important role.Документ Features of the aminomethylation of 7-hydroxy-4'-fluoroisoflavones with primary amines(2010) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, VolodimirThe behavior of 7-hydroxy-4'-fluoroisoflavones under the conditions of the Mannich reaction with primary amines was studied. New 9-alkyl-substituted 3-(4-fluorophenyl)-9,10-dihydro-4H,8H-chromeno-[8,7-e][1,3]oxazin-4-ones were synthesized. A method was developed for the synthesis of 8-amino- methyl derivatives of isoflavones.Документ One-Pot Synthesis of B-Ring ortho-Hydroxylated Homoisoflavonoids(2019) Myshko, Nataliia; Bondarenko, Svetlana; Mrug, Galyna; Sviripa, Vitaliy; Frasinyuk, MihayloA reliable method for the synthesis of B-ring hydroxylated homoisoflavonoids and 3-hetarylmethyl chromones has been developed. The method involves an initial oxa-Diels-Alder reaction of ortho-quinone methides generated from aryl/hetaryl-substituted ortho-(N,N-dimethylaminomethyl)phenols with (2E)-3-(N,N-dimethylamino)-1-(2-hydroxyphenyl)-prop-2-en-1-ones and the subsequent cascade of reactions. This synthetic strategy avoids conventional multistep protocols and does not require the protection of hydroxyl groups, thus allowing the facile synthesis of a library of various aromatic and heterocyclic analogs of naturally occurring homoisoflavonoidsДокумент Reaction of analogs of natural isoflavonoids with amidines(2006) Frasinyuk, Mihaylo; Bondarenko, Svetlana; Khilya, VolodimirRecyclization of the chromone ring in a series of analogs of natural isoflavonoids by reaction with amidines was studied.Документ Reaction of ortho-Quinone Methides with Amphiphilic Nucleophiles(2023) Myshko, Andrii; Mrug, Galyna; Myshko, Ivan; Bondarenko, Svetlana; Frasinyuk, MihayloIn continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, we studied the reaction of isoflavonoid derivatives with amphiphilic nucleophiles with heterocyclic cores. The direction of the reaction significantly depends on starting phenols, nucleophiles, and reaction conditions. Thus, applying phenolic Mannich bases led to formation of isoflavone-heterocycle hybrid via thermal formation of ortho-quinone methides in aprotic solvents and subsequent Michael additionДокумент Regiospecific synthesis of 4,5-diarylisoxazoles bearing cytisine moiety(2015) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, Volodimir; Vinogradova, ValentinaДокумент Synthesis and properties of 4-(3-amino-2-benzofuranyl)-coumarins(2009) Frasinyuk, Mihaylo; Gorelov, S.; Bondarenko, Svetlana; Khilya, VolodimirThe alkylation of o-cyanophenol by 4-chloromethylcoumarins and subsequent intramolecular condensation by the cyano and methylene groups gives substituted 4-(3-amino-2-benzofuranyl) coumarins. We studied the reactions of these compounds with acylating agents as well as with aldehydes, which lead to the 6H-[1]benzofuro[3,2-b]chromeno[4,3-d]pyridin-6-one system as the result of consecutive transformations.Документ Synthesis and properties of 4-chloromethyl-6-hydroxycoumarins and 4-(2-benzofuryl)-6-hydroxycoumarins(2009) Frasinyuk, Mihaylo; Bondarenko, Svetlana; Khilya, VolodimirNew 4-chloromethyl-6-hydroxycoumarins have been obtained by the condensation of hydroquinone derivatives with 4-chloroacetoacetic ester, and have been used for the synthesis of 4-(2-benzofuryl)-6-hydroxycoumarins. Alkylation and acylation of the phenolic hydroxyl of the synthesized 4-(2-benzofuryl)coumarins have been investigated.Документ Synthesis and transformation of 6-aminomethyl derivatives of 7-hydroxy-2-fluoroisoflavones(2020) Makarenko, Olexandr; Bondarenko, Svetlana; Mrug, Galyna; Frasinyuk, MihayloMannich aminomethylation of 8-methyl-7-hydroxy-2'-fluoroisoflavones applying bis-(N,N-dimethylamino) methane afforded C-6 substituted N,N-dimethylaminomethyl derivatives. Subsequent acetylation of these compounds in acetic anhydride in the presence of potassium acetate provided access to the corresponding acetoxymethyl derivatives that were converted to hydroxymethyl- and alkoxymethyl-substituted 7-hydroxyisoflavonoids. Addition of 3-(N,N-dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one or 1,3-dimethyl-5-aminopyrazole with thermally generated orthoquinone methides led to hetero-Diels–Alder or Michael adductsДокумент Synthesis of 2H,10H-pyrano[2,3-f]chromen-2,10-diones and coumarinpyrazole or coumarin-pyrimidine hybrids based on them(2023) Myshko, Nataliia; Mrug, Galyna; Bondarenko, Svetlana; Frasinyuk, MihayloIn the oxa-Diels–Alder reaction of 8-[(2E)-3-(dimethylamino)prop-2-enoyl]-7-hydroxy-2H-chromen-2-one with thermally generated ortho-quinone methides from 2-(N,N-dimethylaminomethyl)phenols and the subsequent cascade of reactions were obtained 2H,10H-pyrano[2,3-f]chromen-2,10-diones. The synthesis of pyrazole–7-hydroxycoumarin hybrids was performed by recyclization of pyranochromone core under hydrazine actions. Reaction of 2H,10H-pyrano[2,3-f]chromen-2,10-diones with guanidine hydrochloride or related N,N-disubstituted derivatives as 1,3-bidentate nucleophiles affords amino-, dimethylamino-, 1-piperidino-, and 4-morpholino substituted pyrimidine-coumarin hybridsДокумент Synthesis of 3',4'-dimethoxyisoflavone derivatives(2003) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, Volodimir2-(Un)substituted-3',4'-dimethoxy-7-hydroxyisoflavones were synthesized. Their derivatives substituted at the phenolic hydroxyl were prepared by alkylation and acylation. Aminomethyl derivatives were also prepared.Документ Synthesis of Coumarin-4-ylethyl Phosphonic Acid Derivatives(2019) Kondratyuk, Kostyantyn; Dluzhevskyi, Viacheslav; Mrug, Galyna; Bondarenko, Svetlana; Brovarets, Volodymyr; Frasinyuk, MihayloWe investigated the reaction of 7-methoxy-4-chloromethylcoumarin and ethyl (diethoxyphosphoryl) acetate in various solvents in the presence of various bases, which led us to the synthesis of ethyl 2-(diethoxyphosphoryl)-3-(7-methoxy-2-oxo-2H-chromen-4-yl) propanoate. It was found that the ratio of 4-chloromethylcoumarin / ethyl (diethoxyphosphoryl) acetate / sodium hydride 1: 2: 2 using dimethylformamide as the solvent was optimal. Alkaline hydrolysis of ester with lithium hydroxide excess affords new 2-(ethoxyphosphoryl)-3-(7-methoxy-2-oxo-2H-chromen-4-yl) propionic acidДокумент Synthesis of formononetin analogs(2003) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, VolodimirDerivatives of the natural isoflavone formononetin were synthesized. Acylation and alkylation of the phenolic hydroxyls and the chromone ring were investigated.Документ Synthesis of Fused Heterocyclic Systems Based on 4-Chloromethylcoumarins(2017) Bondarenko, Svetlana; Frasinyuk, Mihaylo