Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety

doi:10.6023/cjoc201701042

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1542-1547.DOI: 10.6023/cjoc201701042 Previous Articles Next Articles

Notes

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

戴红^a, 陈佳^a, 洪宇^a, 袁斌颖^a, 范崇光^a, 马瑞媛^a, 梁志鹏^b, 石健^b

a. 南通大学化学化工学院南通 226019;
b. 南通大学分析测试中心南通 226019

收稿日期:2017-01-20 修回日期:2017-02-21 发布日期:2017-02-27
通讯作者: 范崇光,石健 E-mail:ntfcg@ntu.edu.cn,gaohbhe2015@aliyun.com
基金资助:
国家自然科学基金（No.21372135）、江苏省“六大人才高峰”（No.2013-SWYY-013）和南通市科技计划（Nos.CP12013002，MS22015020）资助项目.

Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety

Dai Hong^a, Chen Jia^a, Hong Yu^a, Yuan Binying^a, Fan Chongguang^a, Ma Ruiyuan^a, Liang Zhipeng^b, Shi Jian^b

a. College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b. Analysis and Testing Center, Nantong University, Nantong 226019

Received:2017-01-20 Revised:2017-02-21 Published:2017-02-27
Contact: 10.6023/cjoc201701042 E-mail:ntfcg@ntu.edu.cn,gaohbhe2015@aliyun.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (Nos. CP12013002, MS22015020).

1. Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety.PDF(924KB)

Abstract

In order to explore novel pyrazole derivatives with good biological activities, a series of novel pyrazole oxime ester compounds containing pyridyl moiety were designed and synthesized according to the method of active substructure combination. The structures of the target compounds were determined by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay data indicated that some of the title compounds showed certain insecticidal activities. At a concentration of 500 μg/mL, seven compounds exhibited insecticidal activity against Oriental armyworm with 50%~90%, and six compounds exhibited insecticidal activity against Aphis medicaginis with 50%~90%. When the dosage was lowered to 100 μg/mL, 1,3-dimethyl-5-(4-chlorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5f) and 1,3-dimethyl-5-(4-methylphenoxy)pyra-zole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5j) were still active against Aphis medicaginis with inhibitory values of 50% and 50%, respectively. Insecticidal activities against Nilaparvata lugens of 1,3-dimethyl-5-(3-fluorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5b) and 5f were both 100% at 500 μg/mL. Additionally, 1,3-dimethyl-5-(4-fluorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5c), 1,3-dimethyl-5-(3-chlorophenoxy)-pyrazole-4-for-myl-O-(2-chloropyridin-3-formyl)oxime (5e), 1,3-dimethyl-5-(4-trifluoromethoxyphenoxy)pyrazole-4-formyl-O-(2-chloro-pyridin-3-formyl)oxime (5i) and 5j displayed good anti-tumor activity against HepG2 cells with IC₅₀ values of 2.6, 4.6, 1.8和1.1 μmol/L, respectively.

Key words: pyridine, pyrazole, synthesis, biological activity

Cite this article

Dai Hong, Chen Jia, Hong Yu, Yuan Binying, Fan Chongguang, Ma Ruiyuan, Liang Zhipeng, Shi Jian. Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety[J]. Chin. J. Org. Chem., 2017, 37(6): 1542-1547.

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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

Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety

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