Regioselective synthesis of new (imidazo[2,1-b] [1,3]-thiazin-6-yl)-1,2,3-triazole-5-carboxylates as potential antimicrobial agents

Q4 Chemistry

Voprosy Khimii i Khimicheskoi Tekhnologii Pub Date : 2023-10-01 DOI:10.32434/0321-4095-2023-150-5-114-122

N.Yu. Slyvka, L.M. Saliyeva, M.B. Litvinchuk, A.M. Grozav, N.D. Yakovychuk, M.V. Vovk

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引用次数: 0

Abstract

The paper presents the results of the study on the interaction of azido(benz)imidazo[2,1-b][1,3]thiazines with acetylene carboxylates under non-catalytic conditions according to Huguesgen. It was established that the [3+2]-cyclocondensation of the specified reagents occurs regioselectively upon heating and without the use of a catalyst with the formation of a 1,4-addition product, alkyl 1-((benzo)imidazo[2,1-b][1,3]thiazine-6-yl)-1H-1,2,3-triazole-5-carboxylates 4a–g, the structure of which was thoroughly proved by the methods of 1H (13C) NMR spectroscopy and chromatography-mass spectrometry. All obtained compounds were investigated in vitro experiments for antibacterial and antifungal activity. Based on the results of bioscreening, methyl 1-(2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazin-6-yl)-1H-1,2,3- triazole-5-carboxylate 4b, ethyl 1-(2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazin-6-yl)-1H-1,2,3-triazole-5-carboxylate 4c, methyl 1-(3,4-dihydro-2H-benz[4,5]imidazo[2,1-b][1,3]thiazin-3-yl)-1H-1,2,3-triazole-5-carboxylate 4e, tert-butyl 1-(3,4-dihydro-2H-benz[4,5]imidazo[2,1-b][1,3]thiazine-3-yl)-1H-1,2,3-triazole-5-carboxylate 4g showed a bactericidal effect at a concentration of 31.25 g/ml against the bacterium Proteus mirabilis.

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新咪唑[2,1-b][1,3]-噻嗪-6-基)-1,2,3-三唑-5-羧酸盐的区域选择性合成

根据Huguesgen的理论，研究了叠氮(苯)咪唑[2,1-b][1,3]噻嗪与乙炔羧酸盐在非催化条件下的相互作用。通过1H (13C) NMR波谱和色谱-质谱分析，证实了指定试剂在加热条件下，在不使用催化剂的情况下，发生了区域选择性的[3+2]-环缩合反应，生成了1,4加成产物1-((苯并)咪唑[2,1-b][1,3]噻嗪-6-基)-1H-1,2,3-三唑-5-羧酸酯4a-g，其结构得到了充分的证实。对所得化合物进行体外抑菌和抗真菌活性研究。根据生物筛选结果，甲基1-(2,3-二苯基-6,7-二氢- 5h -咪唑[2,1-b][1,3]噻嗪-6-基)- 1h -1,2,3-三唑-5-羧酸盐4b，乙基1-(2,3-二苯基-6,7-二氢- 5h -咪唑[2,1-b][1,3]噻嗪-6-基)- 1h -1,2,3-三唑-5-羧酸盐4c，甲基1-(3,4-二氢- 2h -苯并[2,1-b][1,3]噻嗪-3-基)- 1h -1,2,3-三唑-5-羧酸盐4e，叔丁基1-(3,4-二氢- 2h -苯并[4,5]咪唑[2,1-b][1,3]噻嗪-3-基)- 1h -1,2,3-三唑-5-羧酸酯在浓度为31.25g/ml时对奇异变形杆菌有杀菌作用。

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来源期刊

Voprosy Khimii i Khimicheskoi Tekhnologii Chemical Engineering-Chemical Engineering (all)

CiteScore

0.90

自引率

0.00%

发文量

期刊介绍： Voprosy Khimii i Khimicheskoi Tekhnologii (Issues of Chemistry and Chemical Technology) is published bimonthly by the Ukrainian State University of Chemical Technology and accepts Ukrainian- or English language high-quality original articles and reviews concerning various fields of research in chemistry and chemical engineering. Our unusual title “Voprosy khimii i khimicheskoi tekhnologii” originates from the transliterated initial Russian title “Issues of Chemistry and Chemical Technology“. The fact of the matter is that Voprosy khimii i khimicheskoi tekhnologii was founded in 1965 as a scientific journal mainly for Russian-reading and Russian-speaking readership when «the Iron Curtain» existed. Since 1991, after Ukraine declared its independence, our Journal began to publish the articles in Ukrainian and English. Multilingualism is our established tradition. We remember and cherish our traditions, but we follow the latest trends in modern science. Papers that are multidisciplinary or address new or emerging areas of chemistry and chemical engineering are particularly encouraged. Thus, the scope is dynamic. It includes but is not limited to the traditional areas of general, inorganic, organic, analytical, physical chemistry and electrochemistry, as well as all conventional areas of chemical engineering (chemistry of high molecular compounds, technology of inorganic and organic substances, processing of combustible minerals, chemical technology of silicates, processes and apparatus of chemical productions, etc.). The Journal publishes papers dealing with newer interdisciplinary areas such as materials science, nano-science, catalysis, computational and theoretical chemistry, surface phenomenon and colloidal systems, environmental chemistry, green chemistry.