Synthesis and Phototoxic Activity of Isoxazole and Pyrazoline Derivatives Containing α-Terthiophene

doi:10.6023/cjoc201308008

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (2): 392-397.DOI: 10.6023/cjoc201308008 Previous Articles Next Articles

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三联噻吩-异噁唑、吡唑啉类化合物的合成与光活化性能研究

罗志刚, 刘正勇, 张广龙, 叶杰欣, 杨卓鸿

华南农业大学理学院应用化学系广州 510642

收稿日期:2013-08-06 修回日期:2013-09-29 发布日期:2013-10-11
通讯作者: 杨卓鸿 E-mail:yangzhuohong@aliyun.com
基金资助:
国家自然科学基金（No.21105030）和华南农业大学211三期建设（No.2009B010100001）资助项目.

Synthesis and Phototoxic Activity of Isoxazole and Pyrazoline Derivatives Containing α-Terthiophene

Luo Zhigang, Liu Zhengyong, Zhang Guanglong, Ye Jiexin, Yang Zhuohong

Department of Applied Chemistry, College of Science, South China Agricultural University, Guangzhou 510642

Received:2013-08-06 Revised:2013-09-29 Published:2013-10-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21105030) and the Key Academic Program of 211 Project of South China Agricultural University (No. 2009B010100001).

α-Terthiophene is a class of pesticides with predominant photoactivity. In this work, using terthiophene as the lead compound, the important mediator, 2-carbonyl terthiophene, was synthesized by the carbonylation. After reaction with substituted phenylethanone, terthiophene-substituted α,β-unsaturated ketones were synthesized. Followed by the ring closure reaction with hydroxylamine hydrochloride and hydrazine, a series of 3,5-diaryl isoxazole and 3,5-diaryl pyrazoline drivatives containing α-terthiophene were synthesized, respectively. Their structures were confirmed by ¹H NMR, IR and elemental analysis. The biological activity assay indicated that most of the synthesized compounds exhibit strong photoactivities. In addition, the photoactivities of isoxazole derivatives were much better than those of pyrazoline derivatives, where the photoactivity difference of compound 3b was 64.06 before and after illumination, especially. However, some of the pyrazoline derivatives showed higher activities of killing cells, where the activity of the compound 4d was as high as 83.9%.

Key words: α-terthiophene, isoxazole, pyrazoline, Spodoptera litura (SL) cell line, photoactivity

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Luo Zhigang, Liu Zhengyong, Zhang Guanglong, Ye Jiexin, Yang Zhuohong. Synthesis and Phototoxic Activity of Isoxazole and Pyrazoline Derivatives Containing α-Terthiophene[J]. Chin. J. Org. Chem., 2014, 34(2): 392-397.

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三联噻吩-异噁唑、吡唑啉类化合物的合成与光活化性能研究

Synthesis and Phototoxic Activity of Isoxazole and Pyrazoline Derivatives Containing α-Terthiophene

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