chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2022-17-4-311-322chemicallytech-1859Research ArticleCHEMISTRY AND TECHNOLOGY OF MEDICINAL COMPOUNDS AND BIOLOGICALLY ACTIVE SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ЛЕКАРСТВЕННЫХ ПРЕПАРАТОВ И БИОЛОГИЧЕСКИ АКТИВНЫХ СОЕДИНЕНИЙSynthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamidesСинтез 5-оксиметил-1,2,4-триазол-3-карбоксамидовhttps://orcid.org/0000-0002-5995-5608ГребенкинаЛ. Е.GrebenkinaL. E.

Гребенкина Любовь Евгеньевна, ассистент кафедры биотехнологии и промышленной фармации

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 57189663430

SPIN-код РИНЦ 6518-1280

Lyubov E. Grebenkina, Assistant, Department of Biotechnology and Industrial Pharmacy

86, Vernadskogo pr., Moscow, 119571

Scopus Author ID 57189663430

RSCI SPIN-code 6518-1280

LEGrebenkina@mail.ruhttps://orcid.org/0000-0001-9522-7387ПрутковА. Н.PrutkovA. N.

Прутков Александр Николаевич, аспирант кафедры биотехнологии и промышленной фармации

119571, Москва, пр-т Вернадского, д. 86

ResearcherID G-4025-2016

Scopus Author ID 56228508300

SPIN-код РИНЦ 2965-1335

Alexander N. Prutkov, Postgraduate Student, Department of Biotechnology and Industrial Pharmacy

86, Vernadskogo pr., Moscow, 119571

ResearcherID G-4025-2016

Scopus Author ID 56228508300

RSCI SPIN-code 2965-1335

alex_prutkov@mail.ruhttps://orcid.org/0000-0002-0830-3036МатвеевА. В.MatveevA. V.

Матвеев Андрей Валерьевич, к.х.н., доцент кафедры биотехнологии и промышленной фармации

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 7102723461

SPIN-код РИНЦ 7420-3188

Andrey V. Matveev, Cand. Sci. (Chem.), Associate Professor, Department of Biotechnology and Industrial Pharmacy

86, Vernadskogo pr., Moscow 119571

Scopus Author ID 7102723461

RSCI SPIN-code 7420-3188

4motya@gmail.comhttps://orcid.org/0000-0001-9735-9690ЧудиновМ. В.ChudinovM. V.

Чудинов Михаил Васильевич, к.х.н., доцент кафедры биотехнологии и промышленной фармации

119571, Москва, пр-т Вернадского, д. 86

ResearсherID L-5728-2016

Scopus Author ID 6602589900

SPIN-код РИНЦ 3920-8067

Mikhail V. Chudinov, Cand. Sci. (Chem.), Associate Professor, Department of Biotechnology and Industrial Pharmacy

86, Vernadskogo pr., Moscow 119571

ResearсherID L-5728-2016

Scopus Author ID 6602589900

RSCI SPIN-code 3920-8067

chudinov@mirea.ruМИРЭА - Российский технологический университет (Институт тонких химических технологий им. М.В. Ломоносова)РоссияMIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)Russian Federation202230092022174311322Copyright © Grebenkina L.E., Prutkov A.N., Matveev A.V., Chudinov M.V., 20222022Гребенкина Л.Е., Прутков А.Н., Матвеев А.В., Чудинов М.В.Grebenkina L.E., Prutkov A.N., Matveev A.V., Chudinov M.V.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/1859

Objectives. A key step in the synthesis of natural nucleoside analogs is the formation of a glycosidic bond between the carbohydrate fragment and the heterocyclic base. Glycosylation methods differ in terms of regio- and stereoselectivity. A promising method for the highly specific synthesis of new pharmacologically active compounds involves an enzymatic reaction catalyzed by genetically engineered nucleoside phosphorylases. This study is devoted to the synthesis of a library of analogs of nucleoside heterocyclic bases—5-oxymethyl-1,2,4-triazole- 3-carboxamides—in order to investigate the substrate specificity of genetically engineered nucleoside phosphorylases.Methods. A method of cyclization of acylamidrazones obtained from the single synthetic precursor β-N-tert-butyloxycarbonyl-oxalamidrazone was used to parallel-synthesize new 5-alkoxy/ aryloxymethyl-1,2,4-triazole-3-carboxamides. Silica gel column chromatography was used to isolate and purify the synthesized compounds. A complex of physicochemical analysis methods (nuclear magnetic resonance spectroscopy, chromatography, and mass spectrometry) confirmed the structure of the compounds obtained in the work.Results. 5-alkoxy/aryloxymethyl-1,2,4-triazole-3-carboxamides were obtained to study the substrate specificity of genetically engineered nucleoside phosphorylases. The possibility of obtaining new nucleoside analogs by the chemico-enzymatic method was demonstrated on the basis of preliminary assessment results.Conclusions. The physicochemical characteristics of a series of novel 5-alkoxy/aryloxymethyl- 1,2,4-triazole-3-carboxamides were studied along with their potential to act as substrates for the transglycosylation reaction catalyzed by nucleoside phosphorylases.

Цели. Ключевая стадия синтеза аналогов природных нуклеозидов – образование гликозидной связи между углеводным фрагментом и гетероциклическим основанием. Методы гликозилирования различаются по регио- и стереоселективности. Ферментативная реакция, катализируемая генно-инженерными нуклеозидфосфорилазами – перспективный метод высокоспецифичного синтеза новых фармакологически активных соединений. Данное исследование посвящено синтезу библиотеки аналогов гетероциклических оснований нуклеозидов – 5-оксиметил-1,2,4-триазол-3-карбоксамидов для изучения субстратной специфичности генно-инженерных нуклеозидфосфорилаз.Методы. Для параллельного синтеза новых 5-алкокси/арилоксиметил 1,2,4-триазол3-карбоксамидов применен метод циклизации ациламидразонов, получаемых из единого синтетического предшественника – β-N-третбутилоксикарбонил-оксаламидразона. Для выделения и очистки синтезированных соединений использована колоночная хроматография на силикагеле. Структура полученных в работе соединений подтверждена комплексом методов физико-химического анализа: спектроскопией ядерного магнитного резонанса и хромато-масс-спектрометрометрией.Результаты. Получены 5-алкокси/арилоксиметил-1,2,4-триазол-3-карбоксамиды для изучения субстратной специфичности генно-инженерных нуклеозидфосфорилаз. По результатам предварительной оценки показана возможность получения из них новых аналогов нуклеозидов химико-ферментативным методом.Выводы. Для серии новых 5-алкокси/арилоксиметил-1,2,4-триазол-3-карбоксамидов изучены физико-химические характеристики, а также их способность выступать в роли субстратов реакции трансгликозилирования, катализируемой нуклеозидфосфорилазами.

аналоги нуклеозидов5-оксиметил-124-триазол-3-карбоксамидыпараллельный синтезнуклеозидфосфорилазысубстратная специфичностьnucleoside analogs5-oximethyl-124-triazole-3-carboxamidesparallel synthesisnucleoside phosphorylasesubstrate specificityВыражаем благодарность И.Д. Константиновой, О.С. Смирновой, И.В. Фатееву и другим сотрудникам лаборатории биотехнологии ИБХ РАН за проведение первичных испытаний субстратных свойств НФ по отношению к синтезированным соединениям. ЯМР-спектры зарегистрированы при использовании оборудования Центра коллективного пользования РТУ МИРЭА (соглашение № 075-15-2021-689 от 01.09.2021, уникальный идентификационный номер 2296.61321Х0010).We are grateful to I.D. Konstantinova, O.S. Smirnova, I.V. Fateev, and other employees of the Laboratory of Biotechnology of the IBCh RAS for conducting primary tests of the NP substrate properties in relation to synthesized compounds. 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The authors declare that there are no conflicts of interest present.