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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 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 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 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 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 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 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 pseudobaptigenin analogs(2003) Bondarenko, Svetlana; Frasinyuk, Mihaylo; Khilya, VolodimirHomologs of the natural isoflavonoid pseudobaptigenin containing benzodioxane and benzodioxepane fragments were synthesized. Methanesulfonyl, carbamoyl, aminomethyl, and coumarin-containing isoflavone derivatives were prepared.Документ 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.