chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2021-16-2-156-166chemicallytech-1699Research ArticleCHEMISTRY AND TECHNOLOGY OF MEDICINAL COMPOUNDS AND BIOLOGICALLY ACTIVE SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ЛЕКАРСТВЕННЫХ ПРЕПАРАТОВ И БИОЛОГИЧЕСКИ АКТИВНЫХ СОЕДИНЕНИЙSynthesis of ethers containing 1,3-dioxolane and gem-dichlorocyclopropane fragmentsСинтез простых эфиров, содержащих 1,3-диоксолановый и гем-дихлорциклопропановый фрагментыhttps://orcid.org/0000-0002-1938-1478ДжумаевШ. Ш.DzhumaevSh. Sh.

аспирант кафедры общей, аналитической и прикладной химии,

450064, г. Уфа, ул. Космонавтов, д. 1

Postgraduate Student, Department of General, Analytical and Applied Chemistry, 

1, Kosmonavtov ul., Ufa, 450064

Shakhob2993@mail.ruhttps://orcid.org/0000-0001-6452-9454БорисоваЮ. Г.BorisovaYu. G.

к.х.н. преподаватель кафедры общей, аналитической и прикладной химии,

450064, г. Уфа, ул. Космонавтов, д. 1

Cand. Sci. (Chem.), Teacher, Department of General, Analytical and Applied Chemistry, 

1, Kosmonavtov ul., Ufa, 450064

yulianna_borisova@mail.ruhttps://orcid.org/0000-0001-9770-5434РаскильдинаГ. З.Raskil’dinaG. Z.

к.х.н., доцент кафедры общей, аналитической и прикладной химии,

450064, г. Уфа, ул. Космонавтов, д. 1

Cand. Sci. (Chem.), Associate Professor, Department of General, Analytical and Applied Chemistry, 

1, Kosmonavtov ul., Ufa, 450064

graskildina444@mail.ruhttps://orcid.org/0000-0001-7056-7895КузьминаУ. Ш.KuzminaU. Sh.

к.б.н., научный сотрудник, 

450054, г. Уфа, пр. Октября, д. 71

Cand. Sci. (Biol.), Researcher, Institute of Biochemistry and Genetics, 

71, Oktyabrya pr., Ufa, 450054

ulia-bio@yandex.ruhttps://orcid.org/0000-0001-8673-5240ДаминевР. Р.DaminevR. R.

д.т.н., профессор, директор филиала в г. Стерлитамак,

453118, г. Стерлитамак, Октября пр-т, д. 2

Dr. Sci. (Eng.), Professor, Director of Branch in Sterlitamak, 

2, Oktyabrya pr., Sterlitamak, 453118

daminew@mail.ruhttps://orcid.org/0000-0001-6365-5010ЗлотскийС. С.ZlotskiiS. S.

д.х.н., заведующий кафедрой общей, аналитической и прикладной химии,

450064, г. Уфа, ул. Космонавтов, д. 1

Dr. Sci. (Chem.), Professor, Head of the Department of General, Analytical and Applied Chemistry,

1, Kosmonavtov ul., Ufa, 450064

nocturne@mail.ruУфимский государственный нефтяной технический университетРоссияUfa State Petroleum Technological UniversityRussian FederationИнститут биохимии и генетики УФИЦ РАНРоссияInstitute of Biochemistry and Genetics, Ufa Federal Research Center, Russian Academy of SciencesRussian FederationУфимский государственный нефтяной технический университет, филиал в г. СтерлитамакРоссияUfa State Petroleum Technological University, Branch in SterlitamakRussian Federation202124052021162156166Copyright © Dzhumaev S.S., Borisova Y.G., Raskil’dina G.Z., Kuzmina U.S., Daminev R.R., Zlotskii S.S., 20212021Джумаев Ш.Ш., Борисова Ю.Г., Раскильдина Г.З., Кузьмина У.Ш., Даминев Р.Р., Злотский С.С.Dzhumaev S.S., Borisova Y.G., Raskil’dina G.Z., Kuzmina U.S., Daminev R.R., Zlotskii S.S.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/1699Objectives

Objectives. This study aimed to obtain ethers containing gem-dichlorocyclopropane and 1,3-dioxolane fragments and evaluate their cytotoxic properties against HEK293, SH-SY5Y, MCF-7, and A549 cell lines.

Methods

Methods. The qualitative and quantitative compositions of the reaction masses were determined using mass spectrometry (using a Chromatek-Kristall 5000M device with the 2012 National Institute of Standards and Technology, USA database) and nuclear magnetic resonance spectroscopy (using a Bruker AM-500 device with operating frequencies of 500 and 125 MHz).

Results

Results. Ethers containing gem-dichlorocyclopropane and 1,3-dioxolane fragments were synthesized in the presence of a catamine AB catalyst. The structures of the obtained substances were confirmed using gas-liquid chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy. The cytotoxicity of the esters was studied against HEK293, SH-SY5Y, MCF-7, and A549 cell lines.

Conclusions

Conclusions. Ethers containing gem-dichlorocyclopropane and 1,3-dioxolane fragments were obtained in quantitative yields; however, only 4-{[(2,2-dichloro-3-{[(2,2-dichlorocyclopropyl) methoxy]methyl}cyclopropyl)methoxy]methyl}-2,2-dimethyl-1,3-dioxolane exhibited cytotoxic activity against HEK293, SH-SY5Y, MCF-7, and A549 cell lines. 

Цели

Цели. Получить простые эфиры, содержащие гем-дихлорциклопропановый и 1,3-диоксолановый фрагменты и оценить их цитотоксические свойства в отношении клеточных линий HEK293, SH-SY5Y, MCF-7 и A549.

Методы

Методы. Для определения качественного и количественного состава реакционных масс были использованы следующие методы анализа: газожидкостная хроматография (на аппаратно-программном комплексе «Кристалл 2000»), масс-спектрометрия (на приборе «Хроматэк-Кристалл 5000М» с базой NIST 2012), и спектроскопия ядерного магнитного резонанса (ЯМР-спектроскопия) (на приборе «Bruker AM-500» с рабочими частотами 500 и 125 МГц).

Результаты

Результаты. Синтезированы простые эфиры, содержащие гем-дихлорциклопропановый и 1,3-диоксолановый фрагменты в присутствии катализатора катамина АВ. Строение полученных веществ было подтверждено с помощью газожидкостной хроматографии, масс-спектрометрии и ЯМР-спектроскопии. Для эфиров изучена цитотоксическая активность в отношении клеточных линий HEK293, SH-SY5Y, MCF-7 и A549.

Выводы

Выводы. С количественными выходами получены простые эфиры, содержащие гем-дихлорциклопропановый и 1,3-диоксолановый фрагменты. Установлено, что цитотоксическую активность в отношении клеточных линий HEK293, SH-SY5Y, MCF-7 и A549 среди ряда полученных соединений проявляет только 4-{[(2,2-дихлоро-3-{[(2,2-дихлорциклопропил)метокси]метил}циклопропил)метокси]метил}-2,2-диметил-1,3-диоксолан. 

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