| Ugi反应合成4-甲基-1,2,3-噻二唑化合物及其抗烟草花叶病毒活性 |
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| 引用本文： | 付一峰,左翔,范志金,米娜,郑琴香,黄云,王唤,黄杰,BELSKAYA N.P.,BAKULEV V.A.,MORZHERIN Yu.Yu.,PROKHOROVA P.E..Ugi反应合成4-甲基-1,2,3-噻二唑化合物及其抗烟草花叶病毒活性[J].农药学学报,2010,12(4):408-416. |
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| 作者姓名： | 付一峰 左翔 范志金 米娜 郑琴香 黄云 王唤 黄杰 BELSKAYA N.P. BAKULEV V.A. MORZHERIN Yu.Yu. PROKHOROVA P.E. |
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| 作者单位： | 1.四川农业大学 植物病理学系,四川 雅安 625014 |
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| 基金项目： | Foundation of the Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA) (No.MOAPCA200903);National Natural Science Foundation of China (Nos.20872071,20911120069);Key Project of the Tianjin Natural Science Foundation (10JCZDJC17500);The National Key Project for Basic Research (2010CB126105);National Key Technology Research and Development Program(2011BAE06B05) and Common Specialized Research Fund of China Agriculture (nyhyzx3-21,201103016 and 201003029);The Russian Foundation for Basic Research (Nos RFBR 08-03-00376 a and RFBR/NNSF 08-03-92208 a),the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology (No.201002250). |
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| 摘 要： | 为了寻找更多高活性化合物和进行先导结构的衍生,利用Ugi反应设计合成了18个 4-甲基-1,2,3-噻二唑新化合物(I-1~I-18),其结构均经核磁共振氢谱、红外光谱和高分辨质谱的表征和确认。杀菌、抗病毒以及诱导活性的筛选结果表明:目标化合物I-3和I-11抗烟草花叶病毒(TMV)的半叶法活性高于对照药剂病毒唑,I-6的保护活性和钝化活性高于病毒唑,I-12的治疗活性高于病毒唑,I-16的诱导活性高于对照药剂噻酰菌胺;氟原子的引入有利于保持和提高新化合物的抗病毒活性,4-甲基-1,2,3-噻二唑和氟原子是新化合物抗病毒的重要活性亚结构单元。Ugi反应是新农药创制中先导优化的绿色手段。
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| 关 键 词： | Ugi反应 1 2 3-噻二唑 生物活性 抗病毒活性 植物激活剂 |
| 收稿时间： | 2010/9/25 0:00:00 |
| 修稿时间： | 2010/10/26 0:00:00 |
4-Methyl-1,2,3-thiadiazoles synthesized via Ugi reaction with antiviral activity against tobacco mosaic virus |
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| FU Yi-feng,ZUO Xiang,FAN Zhi-jin,MI N,ZHENG Qing-xiang,HUANG Yun,WANG Huan,HUANG Jie,BELSKAYA N.P.,BAKULEV V.A.,MORZHERIN Yu.Yu. and PROKHOROVA P.E..4-Methyl-1,2,3-thiadiazoles synthesized via Ugi reaction with antiviral activity against tobacco mosaic virus[J].Chinese Journal of Pesticide Science,2010,12(4):408-416. |
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| Authors: | FU Yi-feng ZUO Xiang FAN Zhi-jin MI N ZHENG Qing-xiang HUANG Yun WANG Huan HUANG Jie BELSKAYA NP BAKULEV VA MORZHERIN YuYu and PROKHOROVA PE |
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| Institution: | Department of Plant Pathology,Sichuan Agricultural University,Yaan 625104,Sichuan Province,China; The Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA),Beijing 100193,China;State Key Laboratory of Elemento- organic Chemistry,Nankai University,Tianjin 300071,China;The Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA),Beijing 100193,China; State Key Laboratory of Elemento- organic Chemistry,Nankai University,Tianjin 300071,China;State Key Laboratory of Elemento- organic Chemistry,Nankai University,Tianjin 300071,China;State Key Laboratory of Elemento- organic Chemistry,Nankai University,Tianjin 300071,China;Department of Plant Pathology,Sichuan Agricultural University,Yaan 625104,Sichuan Province,China;State Key Laboratory of Elemento- organic Chemistry,Nankai University,Tianjin 300071,China;Department of Plant Pathology,Sichuan Agricultural University,Yaan 625104,Sichuan Province,China;The Ural Federal University Named After the First President of Russia B.N.Yeltsin, Yeltsin UrFU,620002,Ekaterinburg,Russia;The Ural Federal University Named After the First President of Russia B.N.Yeltsin, Yeltsin UrFU,620002,Ekaterinburg,Russia;The Ural Federal University Named After the First President of Russia B.N.Yeltsin, Yeltsin UrFU,620002,Ekaterinburg,Russia;The Ural Federal University Named After the First President of Russia B.N.Yeltsin, Yeltsin UrFU,620002,Ekaterinburg,Russia |
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| Abstract: | 1,2,3-thiadiazoles possess versatile biological activity.In order to conduct lead derivation and find more active new structures,18 novel 4-methyl-1,2,3-thiadiazoles containing active substructure of 3-fluoro-4-methylphenyl were rationally designed and synthesized via Ugi reaction.All new compounds synthesized were confirmed by 1H NMR,IR and HRMS.Bioassay including fungicidal activity,antivirus activity in vitro and in vivo and systemic acquired resistance of the target compounds indicated that these newly synthesized 4-methyl-1,2,3-thiadiazoles I-3 and I-11 were found to show better anti-tobacco mosaic virus (TMV) activity than ribavirin by half juicy robbing method,compound I-6 showed best protective and inactiviation activities,compound I-12 showed best curative acitivity,compound I-16 showed the best systemic acquired resistance.Fluorine atom favored the antivirus activity of the title compounds.The results suggested that 4-methyl-1,2,3-thiadiazole substructure and fluorine were important moieties for the anti-TMV activity of these compounds and Ugi reaction was an interesting potential green synthetic method in novel pesticide development. |
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| Keywords: | Ugi reaction 4-methyl-1 2 3-thiadiazole biological activity antivirus activity elicitor |
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