摘要
在超声辐射和哌啶催化反应条件下,1,3-二氢吲哚-2-酮(1)与芳香醛2a^2m发生Knoevenagel缩合反应,合成了一系列3-芳亚甲基吲哚-2-酮衍生物3a^3m。该方法具有产率高、反应时间短、后处理简单和环境友好等优点,产物通过~1H NMR、^(13)C NMR和HRMS手段进行结构表征,并通过核磁2D NOESY确定了所有化合物几何构型。初步抑菌活性测试结果表明,化合物3d对革兰氏阳性菌具有较好的抑制作用,最小抑菌浓度(MIC)为15.6μg/m L,化合物3f、3g、3h和3k对油菜菌核病菌表现出良好的抑制活性,MIC为62.5μg/m L,与阳性对照多菌灵相当。此外,对此类化合物的构效关系进行了讨论。
A series of 3-arylidene-indolin-2-one derivatives were conveniently synthesized by the Knoevenagel condensation of aromatic aldehydes 2a ~ 2m with 2-dihydroindol-2-one under ultraphonic. This protocol has advantages of higher yield, simple experimental procedures, shorter reaction time, environmentally benign procedure. The structures of all products were determined by 1H NMR, 13C NMR and HRMS spectra, with the configurations confirmed by 2D NOESY analysis. The preliminary biological activities assays indicated that compound 3d possessed significant activities against Gram-positive bacteria with the minimum inhibitory concentration （MIC） of 15.6 μg/mL. Compounds 3f, 3g, 3h and 3k showed significant inhibitory activities against Sclerotiniasclerotiorum with MIC of 62.5 μg/mL, which were comparable with the positive control Carbendazim. In addition, the structure-activity relationship was also discussed.
出处
《化学通报》
CSCD
北大核心
2017年第5期471-476,共6页
Chemistry
基金
陕西省教育厅重点实验室项目(2010JS056
16JS010)资助
