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Information × Registration Number 0222U000129, 0119U100611 , R & D reports Title Synthesis of new fluoro- and phosphoro- organic acyclic and heterocyclic analogs of natural compounds popup.stage_title Head Gerus Ihor I., Кандидат хімічних наук Registration Date 03-01-2022 Organization V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine popup.description2  The aim of the work is structural design and development of methods for synthesis of new and known promising bioactive compounds, in particular, new amino acid derivatives such as γ-aminobutyric and glutamic acids, and other analogues of natural compounds containing fluorine atoms, fluorine-containing groups and phosphonate (phosphate) residues. The reactions of addition of bromodifluorine-containing reagents to alkoxyalkenes under conditions of radical initiation (Na2S2O4) were studied and fluorine-containing acetals were obtained, which are available promising building blocks for the synthesis of difluoromethylene-containing compounds. The use of the obtained ethyl 4,4-diethoxy-2,2-difluorobutanoate for multigram synthesis of 3,3-difluoro-GABA has been demonstrated. A comparison of pKa values for 3-fluoro and 3,3-fluorine-containing GABA with unsubstituted GABA was performed. A new method for the synthesis of CF2-containing amino acids using the addition reaction of bromodifluoroacetate to α, β-unsaturated derivatives of α-amino acids has been developed. γ,γ-difluoroglutamic acid, γ, γ-difluoroglutamine and nor-alkyl difluorocontaining kainic acid analogue, cis- and trans-3-aryl cyclobutanocarboxylic acids were obtained. It was found that the obtained compounds show submicromolar activity, which confirms the possibility of using the cyclobutane fragment as a bioisostere of ethylene bridge. The physicochemical properties of the target cyclobutane-containing amino acids have also been studied in comparison with L-threonine and the corresponding fluorinated derivatives. An approach to the synthesis of fluorocyclobutane-containing derivatives, GABA analogs: γ- and δ-amino acids, monoprotected diamines, amino alcohols and hydroxy acids is proposed, which is based on the desilylating deoxyfluorination of cyclobutane-containing O-TMS-cyanhydrine. Product Description popup.authors Bugera Maksym Ya. Vdovenko Sergiy I. Dolovanyuk Violetta G. Zhuk Yuriy I. Klipkov Аnton А. Kondratov Ivan S. Kulik Irіna B. Logvinenko Ivan G. Romanenko Vadym D. Ruchko Evgenia V. Sorochynsky Oleksandr Ye. Tarasenko Karen V. Fedorenko Оlena А. Feskov Іlia О. Hilchevskiy Oleksandr М. Shaitanova Olena M. popup.nrat_date 2022-03-09 Close