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Registration Number

0217U006893, 0112U007385 , R & D reports

Title

Development of scientific principles to making substituted of elements unsaturated system for synthesis derivatives of aminophosphonic and aminocarboxylic acids which with bioactivity to be given

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Head

Onys'ko Petro Petrovych,

Registration Date

21-12-2017

Organization

Institute of Organic Chemistry National Academy of Sciences of the Ukraine

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The objects of the study are iminophosphonates and iminocarboxylates, fluorocontaining cycloalkylamines; methods for their functionalization and conversion to aminophosphonic and aminocarboxylic acid derivatives. The aim of the work was to develop a scientific methodology for synthesizing biologically important aminocarboxylic, aminophosphonic and gem-bisphosphonic acid derivatives based on the functionalization of highly electrophilic alfa-iminocarboxylates and phosphonates; the determination of the main regularities of their chemical behavior and the search of possibilities for the use of these new building blocks in synthesis, including asymmetric synthesis, of biorelevant acyclic and heterocyclic derivatives bearing pharmacophoric amino carboxylic acid and aminophosphonate fragments. The convenient preparative methods for the synthesis of a wide range of imines of trihalopyruvates and iminophosphonates have been developed. The alfa -imino esters of carboxylic and phosphonic acids have been shown to be perspective building blocks for the preparation of biorelevant important aminophosphonic and aminocarboxylic acids derivatives on their basis. Novel highly reactive low-molecular synthons - NH- and N-trimethylsilylminophosphonates and iminocarboxylates containing fluoroalkyl groups were synthesized. The latter are promising substrates for the design of novel effective drugs and biomedical studies. A number of acyclic and heterocyclic compounds containing a pharmacophoric aminophosphonate or aminocarboxylate fragment and being perspective for the search for new drugs among them have been synthesized by reductive functionalization of iminocarboxylates and iminophosphonates. Simple and effective methods for the synthesis of fluorinated cycloalkylamines have been developed and some synthetic potentialities of these new low-molecular weight building blocks have been found for obtaining biorelevant compounds containing nitrogen- and a fluorinated cycloalkylamine moiety. Simple and effective methods to synthesize fluorinated cycloalkylamines were developed. Synthetic potentialities of these novel low-molecular weight building blocks for the preparation of biorelevant nitrogen-containing compounds bearing fluorinated cycloalkylamine moiety were revealed. The new methodology for fluorination of alfa cycloalkyl- alfa -aminoacids with sulfur tetrafluoride, consisting in preliminary introduction of electron withdrawing trifluoroacetyl group to the nitrogen atom, was elaborated.

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Єленіч Іванна Петрівна
Алексеенко Анатолій Миколайович
Безгубенко Людмила Валеріївна
Бездудний Андрій Васильович
Замулко Катерина Анатоліївна
Кіселева Олена Іванівна
Колотило Микола Васильович
Онисько Петро Петрович
Пустовіт Юрій Митрофанович
Рассукана Юлія Вікторівна
Рожков Володимир Вадимович
Сизоненко Ярослав Анатолійович
Станько Олег Володимирович
Фетеску Катерина Яківна
Чудакова Тетяна Йосипівна
Шалімов Олександр Олександрович

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2020-04-02