新型含吡啶环结构的吡唑肟酯类衍生物的合成与生物活性研究

发布时间：2018-04-15 02:00

本文选题：吡啶 + 吡唑　；参考：《有机化学》2017年06期

【摘要】：为了寻找具有较好生物活性的吡唑类衍生物,通过活性亚结构拼接的方法,设计制备了一系列未见文献报道的含取代吡啶结构的吡唑肟酯化合物.通过~1HNMR、~(13)CNMR和元素分析对目标化合物的结构进行了表征.初步的生物活性测试结果显示,部分化合物表现出一定的杀虫活性.在测试浓度为500μg/mL时,有7个化合物对粘虫的杀灭活性可达60%~100%,6个化合物对蚜虫的杀死率可达50%~90%.当测试浓度降为100μg/mL时,1,3-二甲基-5-(4-氯苯氧基)吡唑-4-甲醛-O-(2-氯吡啶-3-甲酰基)肟(5f)和1,3-二甲基-5-(4-甲基苯氧基)吡唑-4-甲醛-O-(2-氯吡啶-3-甲酰基)肟(5j)对蚜虫仍表现出一定的杀虫活性,其杀死率均为50%.1,3-二甲基-5-(3-氟苯氧基)吡唑-4-甲醛-O-(2-氯吡啶-3-甲酰基)肟(5b)和5f在测试浓度为500μg/mL时对褐飞虱的杀死率均为100%.另外,1,3-二甲基-5-(4-氟苯氧基)吡唑-4-甲醛-O-(2-氯吡啶-3-甲酰基)肟(5c),1,3-二甲基-5-(3-氯苯氧基)吡唑-4-甲醛-O-(2-氯吡啶-3-甲酰基)肟(5e),1,3-二甲基-5-(4-三氟甲氧基苯氧基)吡唑-4-甲醛-O-(2-氯吡啶-3-甲酰基)肟(5i)和5j对人肝癌(Hep G2)细胞株显示出明显的抗肿瘤活性,其IC_(50)值分别为2.6,4.6,1.8和1.1μmol/L.
[Abstract]:In order to find pyrazole derivatives with good biological activity, a series of pyrazoloxime esters containing substituted pyridine structure were designed and prepared by the method of active substructure splicing.The structure of the target compound was characterized by 1H N NMR and elemental analysis.Preliminary bioactivity test results showed that some of the compounds showed certain insecticidal activity.At the test concentration of 500 渭 g/mL, 7 compounds had the activity of killing armyworm, and the killing rate of 6 compounds against aphids could reach 50% and 90% respectively.When the test concentrations were reduced to 100 渭 g/mL, the concentration of pyrazole-4-formaldehyde-2-chloropyridyl) oxime (5f) and 1 (3-dimethyl-5-oxy) 4-methylphenoxy) pyrazole-O-2-chloropyridyl) oxime still showed 5J) against aphids.Certain insecticidal activity,The killing rates of pyrazole-4-formaldehyde-2-chloropyridyl) oxime (5b) and 5f on brown planthopper at the test concentration of 500 渭 g/mL were all 100%.Pyrazole-3-dimethyl-5-fluorophenoxy) pyrazole-4-formaldehyde-2-chloropyridyl-3-formyl) oxime (5cPe) oxime (1) pyrazole-3-dimethyl-5-chlorophenoxy) pyrazole-4-formaldehyde-2-chloropyridine-3-formyl) oxime) oxime 3- dimethyl-5-trifluoromethoxy phenoxy) pyrazole-4- (methyl) -4- () -methylpyrazolyl) pyrazolyl) pyrazole-4methylpyrazole (2-trifluoromethoxy -5-trifluoromethoxy phenoxy) pyrazolyl) pyrazoleAldehydes -O-O- 2-chloropyridine-3-formyl) oxime (5i) and 5j showed significant anti-tumor activity on human hepatoma cell line Hep G2).The ICs / L values were 2.6 渭 mol / L, 1.6 渭 mol / L and 1.1 渭 mol / L, respectively.
【作者单位】：南通大学化学化工学院;南通大学分析测试中心;
【基金】：国家自然科学基金(No.21372135) 江苏省“六大人才高峰”(No.2013-SWYY-013) 南通市科技计划(Nos.CP12013002,MS22015020)资助项目~~
【分类号】：O626

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