vestichИзвестия Национальной академии наук Беларуси. Серия химических наукProceedings of the National Academy of Sciences of Belarus, Chemical Series1561-83312524-2342The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8331-2025-61-2-126-140vestich-955Research ArticleОРГАНИЧЕСКАЯ ХИМИЯORGANIC CHEMISTRYСинтез и изучение противомикробной активности амидов и солей 4-аминоантипирина – производных 1-оксо-1,2,3,6,7,7а-гексагидро-3а,6-эпоксиизоиндол-7-карбоновых кислотSynthesis and study of antimicrobial activity of amides and salts of 4-aminoantipyrine – derivatives of 1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic acidsДикусарЕ. А.DikusarE. A.

Дикусар Евгений Анатольевич – кандидат химических наук, старший научный сотрудник.

ул. Сурганова, 13, 220072, Минск

Evgenij A. Dikusar – Ph. D. (Chemistry), Senior Researcher, Institute of Physical Organic Chemistry of National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

dikusar@ifoch.bas-net.byАкишинаЕ. А.AkishinaE. A.

Акишина Екатерина Александровна – научный сотрудник.

ул. Сурганова, 13, 220072, Минск

Ekaterina A. Akishina – Researcher, Institute of Physical Organic Chemistry of National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

che.semenovaea@mail.ruЖуковскаяН. А.ZhukovskayaN. A.

Жуковская Нелия Александровна – научный сотрудник.

ул. Сурганова, 13, 220072, Минск

Neliy A. Zukovskaya – Researcher, Institute of Physical Organic Chemistry of National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

neliya_zhukovskaya@mail.ruКолесникИ. A.KolesnikI. A.

Колесник Ирина Андреевна – кандидат химических наук, старший научный сотрудник.

ул. Сурганова, 13, 220072, Минск

Irina A. Kolesnik – Ph. D. (Chemistry), Senior Researcher, Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

irynakolesnik93@gmail.comМаргунЕ. Н.MargunE. N.

Маргун Екатерина Николаевна – младший научный сотрудник.

ул. Сурганова, 13, 220072, Минск

Ekaterina N. Margun – Junior Researcher, Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

margynen0555@gmail.comКовальскаяС. С.KovalskayaS. S.

Ковальская Светлана Степановна – кандидат химических наук, старший научный сотрудник.

ул. Сурганова, 13, 220072, Минск

Svetlana S. Koval’skaya – Ph. D. (Chemistry), Senior Researcher, Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

kovalskaya_61@mail.ruМеньшиковаД. И.MenshikovaD. I.

Меньшикова Дарья Игоревна – студент.

ул. Миклухо-Маклая, 6, 117198, Москва

Daria I. Menshikova – Student, Peoples’ Friendship University of Russia (RUDN University).

6, Miklukho-Maklay Str., 117198, Moscow

daaurum947@gmail.comАлексееваК. А.AlekseevaK. A.

Алексеева Ксения Александровна – аспирант.

ул. Миклухо-Маклая, 6, 117198, Москва

Kseniia A. Alekseeva – Postgraduate Student, Peoples’ Friendship University of Russia (RUDN university).

6, Miklukho-Maklay Str., 117198, Moscow

ka_alekseeva@mail.ruКонцеваяИ. И.KontsevayaI. I.

Концевая Ирина Ильинична – кандидат биологических наук, доцент кафедры.

ул. Советская, 104, 246028, Гомель

Irina I. Kontsevaya – Ph. D. ( Biology), Associate Professor of the Department, Francisk Skorina Gomel State University.

104, Sovetskaya Str., 246028, Gomel

ikantsavaya@mail.ruПоткинВ. И.PotkinV. I.

Поткин Владимир Иванович – доктор химических наук, профессор, академик, заведующий лабораторией.

ул. Сурганова, 13, 220072, Минск

Vladimir I. Potkin – Dr. Sc. (Chemistry), Professor, Academician, Head of the Laboratory, Institute of Physical Organic Chemistry of National Academy of Sciences of Belarus.

13, Surganov Str., 220072, Minsk

potkin@ifoch.bas-net.byИнститут физико-органической химии Национальной академии наук БеларусиInstitute of Physical Organic Chemistry of the National Academy of Sciences of BelarusРоссийский университет дружбы народов имени Патриса ЛумумбыRussian Peoples’ Friendship University named after Patrice LumumbaГомельский государственный университет имени Франциска СкориныFrancisk Skorina Gomel State University202529052025612126140Copyright © Дикусар Е.А., Акишина Е.А., Жуковская Н.А., Колесник И.A., Маргун Е.Н., Ковальская С.С., Меньшикова Д.И., Алексеева К.А., Концевая И.И., Поткин В.И., 20252025Дикусар Е.А., Акишина Е.А., Жуковская Н.А., Колесник И.A., Маргун Е.Н., Ковальская С.С., Меньшикова Д.И., Алексеева К.А., Концевая И.И., Поткин В.И.Dikusar E.A., Akishina E.A., Zhukovskaya N.A., Kolesnik I.A., Margun E.N., Kovalskaya S.S., Menshikova D.I., Alekseeva K.A., Kontsevaya I.I., Potkin V.I.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestichem.belnauka.by/jour/article/view/955

Конденсацией 1-оксо-1,2,3,6,7,7а-гексагидро-3а,6-эпоксиизоиндол-7-карбоновых кислот с 4-аминоантипирином или N-метил-1-[5-(р-толил)изоксазол-3-ил]метиламином в присутствии дициклогексилкарбодиимида в среде дихлорметана были синтезированы соответствующие амиды с выходом 67−78 %. Взаимодействием 1-оксо-1,2,3,6,7,7а-гексагидро-3а,6-эпоксиизоиндол-7-карбоновых кислот с 4-аминоантипирином или N-метил-1-[5-(р-толил)изоксазол-3-ил]метиламином в метаноле были получены соответствующие аммонийные соли с выходом 93−97 %. Проведено квантово-химическое моделирование энергетических параметров и электронной структуры синтезированных соединений методом ab initio, с уровнем теории B3LYP1/MIDI с целью предварительной оценки их потенциальных антибактериальных и противовирусных свойств. Изучена противомикробная активность синтезированных соединений по отношению к штаммам Staphylococcus aureus ATCC 6538 и Escherichia coli АТСС 11229.

By the condensation of 1-oxo-1,2,3,6,7,7a-hexahydrohydro3a,6-epoxyisoindole-7-carboxylic acids with 4-aminoantipyrine or N-methyl-1-[5-(p-tolyl)isodiesol-3-yl]methylamine in the presence of dicyclohexylbisodiimidine in a dichloromethane medium, corresponding amides with a yield of 67–78 % were synthesized. By the interaction of 1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoisoindole-7-carboxylic acids with 4-aminoantipyrine or N-methyl-1-[5-(p-tolyl)isodioxol-3-yl]methylamine in methanol, corresponding ammonic salts with a yield of 93–97 % were obtained. Quantumchemical modelling of energy parameters and electronic structure of synthesized compounds by ab initio method, with the level of theory B3LYP1/MIDI, was carried out in order to preliminary assess their potential antibacterial and antiviral properties. The antimicrobial activity of the synthesized compounds against the strains Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229 was studied.

1-оксо-123677а-гексагидро-3а6-эпоксиизоиндол-7-карбоновые кислоты4-аминоантипиринN-метил-1-[5-(р-толил)изоксазол-3-ил]метиламинацилированиедициклогексилкарбодиимидаммонийные соликвантово-химическое моделированиепротивомикробная активность1-oxo-123677a-hexahydro3а6-epoxyisoisoindol-7-carboxylic acids4-aminoantipyrineN-methyl-1-[5-(p -tolyl)isodioxol-3-yl]methylamineacylationdicyclohexylsilycarboximideammonium saltsquantum-chemical modellingantimicrobial activityРабота выполнена при финансовой поддержке Российского научного фонда (проект № 23-43-10024) и Белорусского республиканского фонда фундаментальных исследований, грант № Х23РНФ-051.The work was carried out with the financial support from the Russian Science Foundation (project No. 23-43-10024) and the Belarusian Republican Foundation for Fundamental Research, grant No. X23РНФ-051.ReferencesCsende, F. A Review on Antibacterial Activity of Some Isoindole Derivatives / F. Csende, A. 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The authors declare that there are no conflicts of interest present.