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2012 , Vol. 32 >Issue 06: 1077 - 1083

DOI: https://doi.org/10.6023/cjoc1111171

研究论文

α-萜品烯马来酰亚胺基酰腙衍生物的合成及杀菌活性研究

  • 马献力 ,
  • 黄建新 ,
  • 段文贵 ,
  • 莫启进 ,
  • 林桂汕 ,
  • 黄翊
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  • a 广西大学化学化工学院 南宁 530004
    b 桂林医学院药学院 桂林 541004

收稿日期: 2011-11-17

  修回日期: 2012-03-08

  网络出版日期: 2012-03-09

基金资助

广西自然科学基金(No. 2010GXNSFB013016)、广西大学科研基金(No. XJZ100245)和广西大学国家大学生创新性实验计划(No. 200924)资助项目.

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Synthesis and Fungicidal Activity of α-Terpinene-maleimide-based acylhydrazone Derivatives

  • Ma Xianli ,
  • Huang Jianxin ,
  • Duan Wengui ,
  • Mo Qijin ,
  • Lin Guishan ,
  • Huang Yi
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  • a College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
    b College of Pharmacy, Guilin Medical University, Guilin 541004

Received date: 2011-11-17

  Revised date: 2012-03-08

  Online published: 2012-03-09

Supported by

Project supported by the Natural Science Foundation of Guangxi Province (No. 2010GXNSFB013016), the Scientific Research Foundation of Guangxi University (No. XJZ100245) and the National Innovation Plan for Undergraduates in Guangxi University (No. 200924).

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摘要

以α-蒎烯为原料,在质子酸催化下发生Wagner-Meerwein 重排得到α-萜品烯,再与马来酸酐发生Diels-Alder 环加成反应得到α-萜品烯马来酸酐3,然后与水合肼反应制备N-氨基-α-萜品烯马来酰亚胺4. 在冰醋酸催化下,4与各种取代苯甲醛反应,合成得到17 个新型α-萜品烯马来酰亚胺基酰腙化合物5a～5q. 初步探索了合成条件,并利用元素分析、1H NMR、13C NMR、LC-MS、FT- IR 等多种手段对目标产物作了分析表征. 初步的生物活性测试表明,大部分化合物具有一定的杀菌活性,其中化合物5n 在浓度为50 mg/L 时对苹果轮纹病菌、花生褐斑病菌和番茄早疫病菌的抑制率分别达91%、 83.3%和76.7%.

关键词： α-蒎烯; N-氨基-α-萜品烯马来酰亚胺; α-萜品烯马来酰亚胺基酰腙; 合成; 杀菌活性

本文引用格式

马献力 , 黄建新 , 段文贵 , 莫启进 , 林桂汕 , 黄翊 . α-萜品烯马来酰亚胺基酰腙衍生物的合成及杀菌活性研究[J]. 有机化学, 2012 , 32(06) : 1077 -1083 . DOI: 10.6023/cjoc1111171

Abstract

In this paper, α-pinene was converted into α-terpinene by Wagner-Meerwein rearrangement under catalysis of protonic acid, followed by Diels-Alder cycloaddtion reaction of α-terpinene with maleic anhydride to obtain α-terpinene-maleic anhydride adduct 3. Then, N-amino-α-terpinene -maleimide 4 was prepared by the reaction of compound 3 with hydrazine hydrate. Seventeen novel α-terpinene-maleimidebased acylhydrazones 5a～5q were synthesized by the reaction of compound 4 with substituted phenyl aldehydes under catalysis of glacial acetic acid. The synthetic conditions were investigated preliminarily. The target compounds were analyzed and characterized by means of elemental analysis, 1H NMR, 13C NMR, LC-MS, and FT-IR. The preliminary bioassay showed that most of the title compounds exhibited a certain fungicidal activity, in which compound 5n had inhibition rates of 91%, 83.3%, and 76.7% against Physalospora piricola, Cercospora rachidicola, and Alternaria solani, respectively, at the concentration of 50 mg/L.

Key words： α-pinene; N-amino-α-terpinene-maleimide; α-terpinene-maleimide-based acylhydrazone; synthesis; fungicidal activity

参考文献

[1] Aggarwal, N.; Kumar, R.; Srivastva, C.; Dureja, P.; Khurana, J. M.J. Agric. Food Chem. 2010, 58, 3056.  
[2] Ye, Y.; Zhao, Z.-G.; Liu, X.-L.; Li, Q.-H. Chin. J. Org. Chem.2009, 29, 993 (in Chinese).(叶英, 赵志刚, 刘兴利, 李清寒, 有机化学, 2009, 29, 993.)
[3] Yang, J.-G.; Pan, F.-Y.; Li, J.-M. Chin. J. Inorg. Chem. 2005, 21,1593 (in Chinese).(杨健国, 潘富友, 李钧敏, 无机化学学报, 2005, 21, 1593.)
[4] Yang, J.-F.; Tao, J.; Li, B.-Q.; Xue, M.; Wei, W.-Z. Chin. J. Synth.Chem. 2009, 17, 151 (in Chinese).(杨金凤, 陶晶, 李炳奇, 薛梅, 韦文珍, 合成化学, 2009, 17,151.)
[5] Wang, D.-L.; Xu, J.; Han, S.; Gu, Z. Chin. J. Org. Chem. 2008, 28,2016 (in Chinese).(王道林, 徐姣, 韩珊, 谷峥, 有机化学, 2008, 28, 2016.)
[6] Long, D.-Q.; Li, D.-J.; Cai, W.-Q.; Chen, S.-S. Chem. Res. Appl.2007, 19, 1246 (in Chinese).(龙德清, 李德江, 蔡卫权, 陈胜胜, 化学研究与应用, 2007, 19,1246.)
[7] Avila, C. M.; Lopes, A. B.; Goncalvesd, A. S.; Silva, L. L.;Romeiro, N. C.; Miranda, A. L. P.; Sant'Anna, C. M. R.; Barreiro,E. J.; Fraga, C. A. M. Eur. J. Med. Chem. 2011, 46, 1245.
[8] Tributino, J. L. M.; Duarte, C. D.; Corrêa, R. S.; Doriguetto, A. C.;Ellena, J.; Romeiro, N. C.; Castro, N. G.; Miranda, A. L. P.; Barreiro,E. J.; Fraga, C. A. M. Bioorg. Med. Chem. 2009, 17, 1125.  
[9] Romeiro, N. C.; Aguirre, G.; Hernández, P.; González, M.; Cerecetto,H.; Aldana, I.; Pérez-Silanes, S.; Monge, A.; Barreiro, E. J.;Lima, L. M. Bioorg. Med. Chem. 2009, 17, 641.  
[10] Lacerda, R. B.; Lima, C. K. F.; Silva, L. L.; Romeiro, N. C.;Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. Bioorg. Med.Chem. 2009, 17, 74.  
[11] Liu, C.-D.; Xia, X.-J.; Yu, L.-J.; Xing, J.-H.; Chen, J.; Peng, W.-L.Agrochemicals 2007, 46, 97 (in Chinese).(刘成荡, 夏旭建, 郁林军, 邢家华, 陈杰, 彭伟立, 农药, 2007,46, 97.)
[12] Bernardino, A. M. R.; Gomes, A. O.; Charret, K. S.; Freitas, A. C.C.; Machado, G. M. C.; Canto-Cavalheiro, M. M.; Leon, L. L.;Amaral, V. F. Eur. J. Med. Chem. 2006, 41, 80.
[13] Huang, M.-Z.; Huang, K.-L.; Chen, C.; Zhang, C.-L.; Wang, Y.-J.Chin. J. Pestic. Sci. 2004, 6, 67 (in Chinese).(黄明智, 黄可龙, 陈灿, 黄路, 张承来, 王永江, 农药学学报,2004, 6, 67.)
[14] Jin, Y. X.; Tan, Z. W.; He, M. Z.; Tian, B. H.; Tang, S. X.; Hewlett,I.; Yang, M. Bioorg. Med. Chem. 2010, 18, 2135.  
[15] Ma, J.-Z.; Wang, H.-B.; Jiang, H. Fine Chem. 2004, 21, 309 (inChinese).(马敬中, 王洪波, 江洪, 精细化工, 2004, 21, 309.)
[16] Wang, J.-P.; Fu, Y.-J.; Yin, W.-P.; Wang, J.-G.; Qin, J.-H. Chin. J.Org. Chem. 2007, 27, 524 (in Chinese).(王建平, 付永举, 尹卫平, 王建革, 秦建华, 有机化学, 2007,27, 524.)
[17] Ma, X.-L.; Chen, L.; Duan, W.-G.; Cen, B.; Dong, S.-Q. Chin. J.Org. Chem. 2011, 31, 1069 (in Chinese).(马献力, 陈丽, 段文贵, 岑波, 董淑求, 有机化学, 2011, 31,1069.)
[18] Mo, Q.-J.; Duan, W.-G.; Li, X.-R.; Huang, D.-P.; Luo, Z.-J. Chin.J. Org. Chem. 2011, 31, 1114 (in Chinese).(莫启进, 段文贵, 李行任, 黄丹平, 罗湛江, 有机化学, 2011,31, 1114.)
[19] Duan, W. G.; Li, X. R.; Mo, Q. J.; Huang, J. X.; Cen, B.; Xu, X. T.;Lei, F. H. Holzforschung 2011, 65, 191.  
[20] Duan, W.-G.; Luo, C.-Q.; Cen, B.; Geng, Z. Chemistry 2007, 70,695 (in Chinese).(段文贵, 罗常泉, 岑波, 耿哲, 化学通报, 2007, 70, 695.)
[21] Zou, R.-X.; Cen, B.; Duan, W.-G.; Ma, X.-L.; Lin, G.-S.; He,Y.-W. J. Guangxi Univ. (Nat. Sci. Ed.) 2011, 36, 463 (in Chinese).(邹荣霞, 岑波, 段文贵, 马献力, 林桂汕, 何宇伟, 广西大学学报(自然科学版), 2011, 36, 463.)
[22] Luo, C.-Q.; Duan, W.-G.; Cen, B.; Ban, L.-N. Biomass Chem. Eng.2006, 40, 25 (in Chinese).(罗常泉, 段文贵, 岑波, 班丽娜, 生物质化学工程, 2006, 40,25.)
[23] Lu, Z.-G.; Kobayashi, N.; Kasai, H. Chem. Reag. 2005, 27, 585 (inChinese).(陆占国, 小林直, 笠井博子, 化学试剂, 2005, 27, 585.)
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