芳脲基酰基硫脲衍生物的固相研磨合成及其植物生长活性

doi:10.3724/SP.J.1095.2013.20578

摘要/Abstract

摘要： 在无溶剂条件下，室温研磨合成了11个未见报道的芳脲基酰基硫脲类化合物，经核磁共振氢谱、红外光谱和元素分析确定结构，并进行了初步的生物活性试验，结果表明，浓度采用10 mg/L时，一些目标化合物具有较好的植物生长调节活性，其中N-苯脲基-N′-肉桂酰基硫脲和N-对甲苯脲基-N′-肉桂酰基硫脲具有较好的生长素活性，分别为54.13%和46.79%；N-对甲苯脲基-N′-肉桂酰基硫脲和N-对甲苯脲基-N′-苯氧乙酰基硫脲具有较好的细胞分裂素活性，分别为55.11%和51.14%。

关键词: 芳脲基酰基硫脲, 固相研磨反应, 生物活性

Abstract: Eleven new arylureido-acylthiourea derivatives have been synthesized by solid phase grinding under solvent-free conditions at room temperature. Their structures were confirmed by 1H NMR, IR and elementary analysis. The results of biological activity tests show that some target compounds have evident activity on plant growth when the concentration is 10 mg/L. Among these, N-phenylureido-N′-cinnamic acylthiourea and N-p-methylphenylureido N′-cinnamic acylthiourea have good auxins activity, the effects are 54.13% and 46.79%, respectively, while N-p-methylphenylureido-N′-cinnamic acylthiourea and N-p-methylphenylureido-N′-phenoxyacetyl thiourea have excellent activity of cytokinin, the effects are 55.11% and 51.14%, respectively.

Key words: arylureido-acylthiourea, solid phase grinding synthesis, biological activity

中图分类号:

O621.3

段志芳, 李充璧, 武旭芳, 陈刚. 芳脲基酰基硫脲衍生物的固相研磨合成及其植物生长活性[J]. 应用化学, DOI: 10.3724/SP.J.1095.2013.20578.

DUAN Zhifang, LI Chongbi*, WU Xufang, CHEN Gang. Solid Phase Grinding Synthesis and Plant Growth Activities of Arylureido-acylthiourea Derivatives[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20578.

参考文献

[1] Takumi M,Takanobu K,Takatoshi I,et al. Synthesis of Aromatic Urea Herbicides by the Selenium-assisted Carbonylation Using Carbon Monoxide with Sulfur[J]. Synth Commun,2000,30(9):1675-1688.

[2] XUE Yan,WU Sizhong,PENG Aidong,et al. Synthesis and Application of Unsymmetrically Substituted Ureas[J]. Chinese J Org Chem,2002,22(8):529-535(in Chinese).

薛燕,吴思忠,彭爱东,等. 非对称取代脲的合成与应用[J]. 有机化学,2002,22(8):529-535.

[3] Pevarello P,Aici R. 2-Ureidothiazole Derivatives Process for Their Preparation and Their Use as Antitumor Agents:WO 0026203[P],2000(132:33445s).

[4] Sekiya T,Moue S. Preparation of Diphenylurea Derivatives for Treatment of Atherosclerosis and Hyperlipemia:EP40525233[P],1991(115: 28916v).

[5] Muraoka M,Ioriya K,Ohashi N. Preparation of Novel Naphthyridine Derivatives as Cholesterol Acyl Transferase Inhibitors:WO 9638445[P],1996(126:89279p).

[6] Ladva K，Patel P，Upadhyay P,et al. Oxadiazoles Part ⅩⅤ.Synthesis and Biological Activities of Substituted l,3,4-Oxadiazole Derivatives[J]. Indian Chem Soc,1996,35:1062.

[7] Kascheres A,Ven J. Preferred Conformations of Some 2-Pyridyl Substituted Thiourea Derivatives[J]. J Hetero Cyclic Chem,1991,28:2057-2058.

[8] ZOU Jinshan,XUE Sijia,GUAN Qian. Study on Synthesis, Property and Biological Activity of Acylthiourea[J]. Chinese J Synth Chem,2001,10(2):109-112(in Chinese).

邹金山,薛思佳,管谦. 酰基硫脲的合成,性质及生物活性[J]. 合成化学,2001,10(2):109-112.

[9] SHENG Chunquan,ZHU Jie,ZHANG Wannian. Synthesis and Antifungal Activity of N-[2-(2,4-Diflurophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl) Propyl]-N′-(4-substituted phenyl)-3-(2H,4H)-1,2,4-triazolones[J]. Chinese Pharm J,2006,41（6）:469-471(in Chinese).

盛春泉,朱杰,张万年. N-[2-(2,4-二氟苯基)-2-羟基-3-(1H-1,2,4-三唑-1-基)丙基]-N′-(4-取代苯基)-3(2H,4H)-1,2,4-三唑酮的合成和抗真菌活性[J]. 中国药学杂志,2006,41（6）:469-471.

[10] DUAN Changqiang,MENG Qingfang,ZHANG Tai,et al,Edrs. Handbook of Modern Chemical Reagents[M]. Beijing:Chemical Industry Press,1988:552(in Chinese).

段长强,孟庆芳,张泰,等编. 现代化学试剂手册[M]. 北京:化学工业出版社,1988:552.

[11] WANG Yangang,GONG Yinxiang,ZHAO Xinyun,et al. Synthesis and Biological Activity of N-5-Tetrazolyl-N′-aryl Formyl Urea[J]. Chinese J Org Chem，2003,23（2）:195-197(in Chinese).

汪焱钢,龚银香,赵新筠,等. N-5-四唑基-N′-芳甲酰基脲的合成及其生物活性[J]. 有机化学,2003,23（2）:195-197.

[12] LI Yingjun,SUN Yazhen,ZHAO Nan. Syntheses and Characterizations of 1-Arylaminoacetyl-4-arylacetyl Thiosemicarbazides[J]. Chemistry,2010,（5）:469-472(in Chinese).

李英俊,孙亚珍,赵楠,等. 1-芳氨基乙酰基-4-芳乙酰基氨基硫脲的合成及结构表征[J]. 化学通报,2010,（5）:469-472.

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