摘要
【目的】建立3种N-苯基-N′-硝基苯基脲类化合物的氯甲酸甲酯合成法,并对其生物活性进行测定。【方法】在三正丁胺存在下,硝基苯胺与氯甲酸甲酯加热回流生成硝基苯胺基甲酸甲酯,后者再与过量苯胺反应生成N-苯基-N′-硝基苯基脲,通过优化试验对3种脲类化合物的第2步反应条件进行优化,采用红外光谱和质谱对目标化合物进行结构鉴定。以丰光萝卜种子为材料,采用萝卜子叶扩张生长法测定3种化合物的促细胞分裂活性。【结果】建立的氯甲酸甲酯合成法分2步进行,第1步反应很快,回流30 min即可完成。3种化合物第2步反应的最佳条件:N-苯基-N′-(2-硝基苯基)脲,170℃反应4.5 h,产率85.5%;N-苯基-N′-(3-硝基苯基)脲,152℃反应4.0 h,产率95.0%;N-苯基-N-′(4-硝基苯基)脲,165℃反应5.0 h,产率89.1%。3种化合物在0.01~1.00 mg/L均能明显促进萝卜子叶生长,其中N-苯基-N-′(3-硝基苯基)脲的活性最高。【结论】氯甲酸甲酯法具有设备简单、反应步骤少、后处理简便、产物纯度和收率高等优点,适用于实验室和工业生产。带有吸电子基团的二苯基脲可较好地促进萝卜子叶扩张,同一取代基的活性按间位、对位、邻位依次递减。
[Objective] Three kinds of N-phenyl-N′-nitrolphenylureas were successfully synthesized by methyl chloroformate method and their promoting cell division activity was measured. [Method] Nitroanil- ine firstly reacted with methyl chloroformate in the presence of tri-n-butylamine, and then the resulting mixture continued to react with aniline to yield N-phenyl-N′-nitrophenylureas. The best reaction condition of the second step was optimized through the optimization test. The structures of the target compounds were elucidated by IR and MS analysis. The promoting Radish Fengguang cell division activity was tested by the method of radish cotyledon stretching growth. [Result] The first step reaction was finished under reflux for 30 min. The mixture of the first step was refluxed for 4.5 h at 170 ℃ and obtained N-phenyl-N′- (2-nitrophenyl)urea with the yield of 85.5% ,refluxed for 4.0 h at 152 ℃ and got N-phenyl-N′-(3-nitro- phenyl)urea with the yield of 95.0%,and refluxed for 5.0 h at 165 ℃ and got N-phenyl-N′-(4-nitrophenyl) urea with the yield of 89.1%. The compounds above all effectively promoted radish cotyledon growing when their concentrations ranged from 0.01 mg/L to 1. rea showed the highest bioactivity. [Conclusion] This 00 mg/L, of which N-phenyl-N′- (3-nitrophenyl) umethod can be applied in laboratory and industry with the following advantages:simple device, short procedure, easy and simple work-up, pure product and high yield. Diphenylureas with electron-withdrawing groups could promote radish cotyledon growing and the biological activities of their derivatives of the same group decreased gradually according to the order of metaposition,para-position and ortho-position.
出处
《西北农林科技大学学报(自然科学版)》
CSCD
北大核心
2009年第10期188-192,共5页
Journal of Northwest A&F University(Natural Science Edition)
基金
国家自然科学基金项目(30571402
30771454)