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有机化学.pdfVIP

DOI: 10.6023/cjoc201308008 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 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) 摘要 α-三联噻吩(a-T)是一类具有优异性能的光活化农药. 以三联噻吩为先导化合物, 经 a 醛基化制得关键中间体 2- 醛基三联噻吩, 然后与取代苯乙酮反应, 得到三联噻吩取代的 α,β-不饱和酮, 再与盐酸羟胺、水合肼关环, 最终合成两 1 类含 3,5-二芳基异噁唑和 3,5-二芳基吡唑啉的 α-三联噻吩衍生物. 其结构经 H NMR, IR 和元素分析确证. 初步生物活 性测定试验表明, 绝大多数目标化合物具有良好的光活化活性, 异噁唑类衍生物的光活化活性普遍要好于吡唑啉类衍 生物, 其中化合物 3b 光照前后的细胞毒杀活性差异为 64.06 倍. 但部分吡唑啉类衍生物整体显示出较高的细胞毒杀活 性, 其中化合物 4d 光照细胞毒杀活性为 83.9%. 关键词 α-三联噻吩; 异噁唑; 吡唑啉; 斜纹夜蛾卵巢细胞; 光活化活性 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) Abstract 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 substi- tuted phenylethanone, terthiophene-substituted α,β-unsaturated ketones were synthesized. Followed by the ring closure reac- tion with hydroxylamine hydrochloride and hydrazine, a series of 3,5-diaryl isoxazole and 3,5-diaryl pyrazoline drivatives containing α-terthiophene were synthesized, respectively