铜催化的 2-硝基咪唑与芳基硼酸的 Chan-Evans-Lam 偶联反应：一种针对肺炎链球菌的新型生物活性试剂的研究。
Cu-Catalyzed Chan-Evans-Lam Coupling Reactions of 2-Nitroimidazole with Aryl Boronic Acids: An Effort toward New Bioactive Agents against S. pneumoniae.
机构信息
Department of Chemistry, Mississippi State University, Mississippi, MS 39762, US.
Mississippi School for Math and Science, Columbus, MS 39701, US.
出版信息
Chem Biodivers. 2022 Aug;19(8):e202200327. doi: 10.1002/cbdv.202200327. Epub 2022 Aug 3.
The coupling of phenylboronic acids with poorly-activated imidazoles is studied as a model system to explore the use of copper-catalyzed Chan-Evans-Lam (CEL) coupling for targeted C-N bond forming reactions. Optimized CEL reaction conditions are reported for four phenanthroline-based ligand systems, where the ligand 4,5-diazafluoren-9-one (dafo, L2) with 1 molar equivalent of potassium carbonate yielded the highest reactivity. The substrate 2-nitroimidazole (also known as azomycin) has documented antimicrobial activity against a range of microbes. Here N-arylation of 2-nitroimidazole with a range of aryl boronic acids has been successfully developed by copper(II)-catalyzed CEL reactions. Azomycin and a range of newly arylated azomycin derivatives were screened against S. pneumoniae, where 1-(4-(benzyloxy)phenyl)-2-nitro-1H-imidazole (3d) was demonstrated to have a minimal inhibition concentration value of 3.3 μg/mL.
将苯硼酸与活化不良的咪唑偶联作为模型体系进行研究，以探索铜催化的 Chan-Evans-Lam（CEL）偶联在靶向 C-N 键形成反应中的应用。本文报道了四种菲咯啉配体系统的优化 CEL 反应条件，其中配体 4,5-二氮杂芴-9-酮（dafo，L2）与 1 摩尔当量的碳酸钾反应活性最高。2-硝基咪唑（也称为氮霉素）具有针对多种微生物的抗菌活性。在此，通过铜（II）催化的 CEL 反应成功地开发了 2-硝基咪唑与一系列芳基硼酸的 N-芳基化反应。对氮霉素和一系列新的氮霉素衍生物进行了针对 S. pneumoniae 的筛选，其中 1-(4-(苄氧基)苯基)-2-硝基-1H-咪唑（3d）的最小抑制浓度值为 3.3 μg/mL。
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