danДоклады Национальной академии наук БеларусиDoklady of the National Academy of Sciences of Belarus1561-83232524-2431The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8323-2018-62-3-293-297dan-520Research ArticleХИМИЯCHEMISTRYСИНТЕЗ И АНТИБАКТЕРИАЛЬНАЯ АКТИВНОСТЬ НЕКОТОРЫХ 1,4- И 1,4,5-ЗАМЕЩЕННЫХ-1H-1,2,3-ТРИАЗОЛОВ ПО ОТНОШЕНИЮ К ШТАММУ STAPHYLOCOCCUS AUREUSSYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME 1,4- AND 1,4,5-SUBSTITUTED-1H-1,2,3TRIAZOLES IN RELATION TO THE STAPHYLOCOCCUS AUREUS STRAINЗураевА. В.ZuraevA. V.

Зураев Александр Викторович – мл. науч. сотрудник.

ул. Ленинградская, 14, 220050, Минск.

Zuraev Alexander Victorovich – Junior researcher. 

14, Leningradskaya Str., 220030, Minsk.

alex.zuraev@gmail.comЛишайА. В.LishaiA. V.

Лишай Анастасия Викторовна – ассистент. 

пр. Дзержинского, 83, 220116, Минск.

Lishai Anastasia Victorovna – Assistant.

83, Dzerzhinsky Ave., 220116, Minsk.

nastassia.lishai@gmail.comГригорьевЮ. В.GrigorievYu. V.

Григориев Юрий Викторович – канд. хим. наук, заведующий лабораторией. 

ул. Ленинградская, 14, 220050, Минск.

Grigoriev Yuri Victorovich – Ph. D. (Chemistry), Head of Laboratory.   

14, Leningradskaya Str., 220030, Minsk.

azole@bsu.byИвашкевичО. А.IvashkevichO. A.

Ивашкевич Олег Анатольевич – академик, д-р хим. наук, профессор, первый проректор.

пр. Независимости, 4, 220030, Минск.

Ivashkevich Oleg Anatolievich – Academician, D. Sc. (Chemistry), Professor, First prorector. 

4, Nezavisimosti Ave., 220030, Minsk.

IvashkevichO@bsu.byНаучно-исследовательский институт физико-химических проблем Белорусского государственного университета.Research Institute for Physical Chemical Problems of the Belarusian State University.Белорусский государственный медицинский университетBelarusian State Medical University .Белорусский государственный университет.Belarusian State University.201828062018623293297Copyright © Зураев А.В., Лишай А.В., Григорьев Ю.В., Ивашкевич О.А., 20182018Зураев А.В., Лишай А.В., Григорьев Ю.В., Ивашкевич О.А.Zuraev A.V., Lishai A.V., Grigoriev Y.V., Ivashkevich O.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://doklady.belnauka.by/jour/article/view/520

С использованием модифицированной каталитической системы для реакции Хьюзгеновского [3+2]-циклоприсоединения получен ряд 1,4- и 1,4,5-замещенные-1Н-1,2,3-триазолов. Установлено, что синтезированные производные 1H-1,2,3-триазолов проявляют высокую антибактериальную активность в отношении патогенного штамма Staphylococcus aureus, сопоставимую с широко используемым в клинической практике антибиотиком «Цефотаксим».

A number of 1,4- and 1,4,5-triazoles have been synthesized using a modified catalytic system for the Huisgen [3+2] cycloaddition reaction. The bactericidal activity of the synthesized compounds has been studied. The synthesized derivatives of 1H-1,2,3-triazoles have demonstrated higher antibacterial activities in relation to the pathogen Staphylococcus aureus strain which can be comparable with the clinically used antibiotic “Cefotaxime”.

цефотаксимStaphylococcus aureus1H-123-триазолыбиоактивностьнаночастицы медиCefotaximeStaphylococcus aureus1H-123-triazolesbioactivitycopper nanoparticlesReferencesSynthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry / C. F. Ye [et al.] // Org. Lett. – 2007. – Vol. 9, N 19. – P. 3841–3844. https://doi.org/10.1021/ol701602aYe C. F., Gard G. L., Winter R. W., Syvret R. G., Twamley B., Shreeve J. M. Synthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry. Organic Letters, 2007, vol. 9, no. 19, pp. 3841–3844. https://doi.org/10.1021/ol701602aOxidative Palladium Catalysis in SNAr Reactions Leading to Heteroaryl Ethers from Pyridotriazol-1-yloxy Heterocycles with Aryl Boronic Acids / S. Wacharasindhu [et al.] // J. Am. Chem. Soc. – 2009. – Vol. 131, N 12. – P. 4174– 4175. https://doi.org/10.1021/ja808622zWacharasindhu S., Bardhan S., Zhao-Kui Wan, Tabei K., Mansour T. S. Oxidative Palladium Catalysis in SNAr Reactions Leading to Heteroaryl Ethers from Pyridotriazol-1-yloxy Heterocycles with Aryl Boronic Acids. Journal of the American Chemical Society, 2009, vol. 131, no. 12, pp. 4174–4175. https://doi.org/10.1021/ja808622zClick Chemistry Reactions in Medicinal Chemistry: Applications of the 1,3-Dipolar cycloaddition between Azides and Alkynes / G. C. Tron [et al.] // Med. Res. Rev. – 2008. – Vol. 28, N 2. – P. 278–308. https://doi.org/10.1002/med.20107Tron G. C., Pirali T., Billington R. A., Canonico P. L., Sorba G., Genazzani A. A. Click Chemistry Reactions in Medicinal Chemistry: Applications of the 1,3-Dipolar cycloaddition between Azides and Alkynes. Medicinal Research Reviews, 2008, vol. 28, no. 2, pp. 278–308. https://doi.org/10.1002/med.20107Substituent Effects on the Antibacterial Activity of Nitrogen-Carbon-Linked (Azolylphenyl)oxazolidinones with Expanded Activity Against the Fastidious Gram-Negative Organisms Haemophilus influenzae and Moraxella catarrhalis / M. J. Genin [et al.] // J. Med. Chem. – 2000. – Vol. 43, N 5. – P. 953–970. https://doi.org/10.1021/jm990373eGenin M. J., Allwine D. A., Anderson D. J., Barbachyn M. R., Emmert D. E., Garmon S. A., Graber D. R., Grega K. C., Hester J. B., Hutchinson D. K., Morris J., Reischer R. J., Ford C. W., Zurenko G. E., Hamel J. C., Schaadt R. D., Stapert D., Yagi B. H. Substituent Effects on the Antibacterial Activity of Nitrogen-Carbon-Linked (Azolylphenyl)oxazolidinones with Expanded Activity Against the Fastidious Gram-Negative Organisms Haemophilus influenzae and Moraxella catarrhalis. Journal of Medicinal Chemistry, 2000, vol. 43, no. 5, pp. 953–970. https://doi.org/10.1021/jm990373eEfficient and tunable synthesis of new polydentate bifunctional chelating agents using click chemistry / C. Camp [et al.] // Tetrahedron Lett. – 2008. – Vol. 49. – P. 1979–1983. https://doi.org/10.1016/j.tetlet.2008.01.086Camp C., Dorbes S., Picard C., Benoist E. Efficient and tunable synthesis of new polydentate bifunctional chelating agents using click chemistry. Tetrahedron Letters, 2008, vol. 49, pp. 1979–1983. https://doi.org/10.1016/j.tetlet.2008.01.086Copper-Polymer Nanocomposite Catalyst for Synthesis of 1,4-Diphenylbutadiyne-1,3 / A. V. Zuraev [et al.] // Z. Anorg. Allg. Chem. – 2017. – Vol. 643, N 19. – P. 1215–1219. https://doi.org/10.1002/zaac.201700213Zuraev A. V., Grigoriev Y. V., Ivashkevich L. S., Lyakhov A. S., Ivashkevich O. A. Copper-Polymer Nanocomposite Catalyst for Synthesis of 1,4-Diphenylbutadiyne-1,3. Zeitschrift für anorganische und allgemeine Chemie, 2017, vol. 643, no. 19, pp. 1215–1219. https://doi.org/10.1002/zaac.201700213Copper-polymer nanocomposite: an efficient catalyst for green Huisgen click synthesis / A. V. Zuraev [et al.] // Tetrahedron Lett. – 2018. – Vol. 59, N 16. – P. 1583–1586. https://doi.org/10.1016/j.tetlet.2018.03.028Zuraev A. V., Grigoriev Y. V., Budevich V. A., Ivashkevich O. A. Copper-polymer nanocomposite: an efficient catalyst for green Huisgen click synthesis. Tetrahedron Letters, 2018, vol. 59, no. 16, pp. 1583–1586. https://doi.org/10.1016/j.tetlet.2018.03.028Государственная фармакопея Республики Беларусь: в 2 т. / Центр экспертиз и испытаний в здравоохранении; под общ. ред. А. А. Шерякова. – Молодечно: Победа, 2012. – Т. 1: Общие методы контроля качества лекарственных средств. – 1220 с.Sheryakov A. A., eds. State Pharmacopoeia of the Republic of Belarus. Vol. 1. General methods of quality control of medicines. Molodechno, Pobeda Publ., 2012. 1220 p. (in Russian).

The authors declare that there are no conflicts of interest present.