| 摘要: |
| [目的]建立N-苯基N′-甲基苯基脲类化合物的合成方法,并分析其生物活性.[方法]在三乙胺存在的条件下,苯胺与氯甲酸甲酯反应生成苯胺基甲酸甲酯,后者不经分离再与过量甲基苯胺反应即可生成N-苯基-N′-甲基苯基脲;采用红外光谱和质谱对目标化合物的结构进行表征,并以丰光萝卜种子为材料,采用萝卜子叶扩张生长法测定其对进细胞分裂的促进活性.[结果]第一步反应回流30 min即可;通过正交试验优化得到第二步反应的条件为:140 ℃回流3.0 h得N-苯基-N′-(4-甲基苯基)脲,产率为87.4%;152 ℃回流4.5 h得N-苯基-N′-(2-甲基苯基)脲,产率为81.5%;155 ℃回流5.5 h得N-苯基-N′-(3-甲基苯基)脲,产率为80.4%.3种化合物的质量浓度为0.01～1.00 mg/L时,均对萝卜子叶的生长有明显的促进作用,其中以1.00 mg/L N-苯基-N′-(3-甲基苯基)脲的活性最高.[结论]氯甲酸甲酯法具有操作方便安全、产率高、后处理简单和"一锅煮"等优点,适于实验室和工业生产使用.3个甲基取代的二苯基脲类化合物均可较好地促进萝卜子叶的扩张,其活性按间位、对位和邻位依次递减. |
| 关键词: 二苯基脲 N-苯基-N'-甲基苯基脲 有机合成 生物活性 |
| DOI： |
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| 基金项目:国家自然科学基金 |
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| Study on the Synthesis and Biological Activity of N-Phenyl-N′-Methylphenylureas |
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| Abstract: |
| 【Objective】 The study was to establish the synthesis method of N-phenyl-N′-methylpenylureas and to analyze their biological activity. 【Method】 Three kinds of N-phenyl-N′-methylphenylureas were successfully prepared by methyl chloroformate method,the synthetic procedure went as follows:first,aniline reacted with methyl chloroformate in the presence of triethylamine,then the resulted mixture continued to react with methylaniline to provide N-phenyl-N′-methylphenylureas.Their structures were elucidated by IR and MS spectrometry.Their biological activity of promoting Radish Fengguang cell split was tested by the method of radish cotyledon stretching growth. 【Result】The first step just enabled the reagents reflux for 30 min.Their best reaction conditions of the second step were confirmed by the orthogonal experiment.The yield of N-phenyl-N′(4-methylphenyl)urea was 87.4% when the reagents were refluxed for 3.0 h at 140 ℃,the yield of N-phenyl-N′(2-methylphenyl) 81.5% when the reagents refluxed for 4.5 h at 152 ℃,the yield of N-phenyl-N′(3-methylphenyl) 80.4% when the reagents refluxed for 5.5 h at 155 ℃.The compounds above all promoted radish cotyledon growing effectively when the concentration ranged from 0.01-1.00 mg/L.Furthermore,the third one had the highest biological activity at the concentration of 1.00 mg/L. 【Conclusion】 This method can be applied in laboratory and industry for its following advantages:simple devices,short procedure,easy and simple work-up,purer product,high yield.Three diphenylureas all could promote radish cotyledon growing and the biological activities of their derivatives decreased gradually according to the order of meta,para and orthon position. |
| Key words: diphenylurea N-phenyl-N′-methylphenylurea organic synthesis biological activity |
