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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.
In order to find pyrazole derivatives with good biological activity, a series of pyrazole oxime ester compounds with substituted pyridine structure were designed and prepared by means of active substructures splicing.According to ~ 1HNMR, ~ (13 ) CNMR and elemental analysis were used to characterize the structure of the target compounds.The preliminary bioassay results showed that some compounds showed certain insecticidal activity.At the test concentration of 500μg / Inactivation rate can reach 60% ~ 100%, 6 compounds kill aphids up to 50% ~ 90% .When the test concentration is reduced to 100μg / mL, 1,3-dimethyl-5- (2-chloropyridine-3-carbonyl) oxime (5f) and 1,3-dimethyl-5- (4-methylphenoxy) Oxazole (5j) showed some insecticidal activity against aphids, and its killing rate was 50% .1,3-Dimethyl The killing of the brown planthopper (BPH) at the test concentration of 500 μg / mL was carried out using 5- (3-fluorophenoxy) pyrazole-4-carbaldehyde-O- (2-chloropyridine- The rate was 100%, and 1,3-dimethyl-5- (4-fluorophenoxy) pyrazole-4-carbaldehyde-O- (2-chloropyridine- ,1 , 3-dimethyl-5- (3-chlorophenoxy) pyrazole-4-carbaldehyde-O- (2-chloropyridine- 5- (4-Trifluoromethoxyphenoxy) pyrazole-4-carbaldehyde-O- (2-chloropyridine-3-formyl) oxime (5i) and 5j on Hep G2 cell lines The results showed that the IC 50 values were 2.6, 4.6, 1.8 and 1.1 μmol / L, respectively.