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Design, Synthesis and Antibacterial Activity of N-(3-((4-(6-(2,2,2- Trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-yl)amide Derivatives
Asian Journal of Chemistry Pub Date : 2021-02-16 , DOI: 10.14233/ajchem.2021.23039
B. Siva Reddy 1 , K.R.S. Prasad 1
Affiliation  

A new series of N-(3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3- yl)amide derivatives (10a-h)were synthesized by the reaction of 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin- 3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-amine (8) with various carboxylic acids in the presence of T3P catalyst. The reaction is usually furnished within 60 min with good isolated yields. Coupling of 6-(2,2,2-trifluoroethoxy) nicotinic acid (1) with Weinreb amine hydrochloride gave N-methoxy-Nmethyl- 6-(2,2,2-trifluoroethoxy) nicotinamide (2). Compound 3 was synthesized by the Grignard reaction of compound 2 with methylmagnesium bromide. Bromination of compound 3 with N-bromo succinamide to obtain 2-bromo-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethan-1-one (4), which was reacted with 2-(3-(((benzyloxy)carbonyl)amino)oxetan-3-yl)acetic acid (5) gave 2-oxo-2-(6-(2,2,2- trifluoroethoxy)pyridin-3-yl)ethyl 2-(3-(((benzyloxy)carbonyl)amino)oxetan-3-yl)acetate (6). Compound 7 was synthesized by the cyclization of compound 6 with ammonium acetate. Finally, debenzylation of compound 7 gave 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2- yl)methyl)oxetan-3-amine (8). All the synthesized amide compounds were characterized by analytical spectral techniques, like 1H & 13C NMR and LCMS and also evaluated their antibacterial activity.

中文翻译:

N-(3-((4-(6-(2,2,2-三氟乙氧基)吡啶-3-基)-1H-咪唑-2-基)甲基)氧杂环丁烷-3-基的设计、合成及抗菌活性)酰胺衍生物

全新系列N-(3-((4-(6-(2,2,2-三氟乙氧基)吡啶-3-基)-1H-咪唑-2-基)甲基)氧杂环丁烷-3-基)酰胺衍生物(10a-h)由3-((4-(6-(2,2,2-三氟乙氧基)吡啶-3-基)-1H-咪唑-2-基)甲基)氧杂环丁烷-3-反应合成胺(8)与各种羧酸在T3P催化剂存在下反应。反应通常在 60 分钟内完成,分离收率良好。6-(2,2,2-三氟乙氧基)烟酸(1)与Weinreb胺盐酸盐偶联,得到N-甲氧基-N甲基-6-(2,2,2-三氟乙氧基)烟酰胺(2)。化合物3是通过化合物2与甲基溴化镁的格氏反应合成的。化合物3与N-溴代琥珀酰胺溴化,得到2-溴-1-(6-(2,2,2-三氟乙氧基)吡啶-3-基)乙烷-1-酮(4),将其与2-反应(3-(((苄氧基)羰基)氨基)氧杂环丁烷-3-基)乙酸(5)得到2-氧代-2-(6-(2,2,2-三氟乙氧基)吡啶-3-基)乙基2 -(3-(((苄氧基)羰基)氨基)氧杂环丁烷-3-基)乙酸酯(6)。化合物7是通过化合物6与乙酸铵环化合成的。最后,化合物7脱苄基得到3-((4-(6-(2,2,2-三氟乙氧基)吡啶-3-基)-1H-咪唑-2-基)甲基)氧杂环丁烷-3-胺(8) 。所有合成的酰胺化合物均通过分析光谱技术(如 1H 和 13C NMR 和 LCMS)进行表征,并评估其抗菌活性。
更新日期:2021-02-16
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