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2013 , Vol. 33 >Issue 07: 1568 - 1572

DOI: https://doi.org/10.6023/cjoc201301068

研究简报

1-{4-[(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-噻唑-2-基}-3-取代苯甲酰基脲类化合物的合成及其生物活性

  • 戴红 ,
  • 赵元飞 ,
  • 牛平 ,
  • 钱翊钧 ,
  • 李永强 ,
  • 方建新 ,
  • 石玉军
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  • a 南通大学化学化工学院 南通 226019;
    b 南开大学元素有机化学研究所 天津 300071

收稿日期: 2013-01-29

  修回日期: 2013-02-07

  网络出版日期: 2013-03-06

基金资助

国家自然科学基金(Nos. 21102077, 21202089);国家级大学生创新训练计划项目(No. 201210304039)和江苏省“六大人才高峰”(No. 2011-SWYY-009)资助项目.

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Synthesis and Biological Activity of 1-{4-[(2-Cyanoimino-1,3-thiazolidine-3-yl)methyl]thiazol-2-yl}-3-aroyl Ureas

  • Dai Hong ,
  • Zhao Yuanfei ,
  • Niu Ping ,
  • Qian Yijun ,
  • Li Yongqiang ,
  • Fang Jianxin ,
  • Shi Yujun
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received date: 2013-01-29

  Revised date: 2013-02-07

  Online published: 2013-03-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21102077, 21202089), the Science and Technology Innovation Foundation for the College Students of China (No. 201210304039) and the Research Foundation of the Six People Peak of Jiangsu Province (No. 2011-SWYY-009).

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摘要

为了从噻唑类化合物中寻找新的活性物质, 利用4-[(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-2-氨基噻唑与芳酰基异氰酸酯的缩合反应, 合成了一系列未见文献报道的新型含酰基脲结构的噻唑类衍生物6. 经1H NMR, MS和元素分析对所有目标化合物的结构进行了表征, 此外, 经13C NMR进一步证实了化合物6a, 6e及6h的结构. 初步生物活性试验结果表明, 在浓度为50 μg/mL时, 部分目标化合物表现出一定的杀菌活性. 如化合物6d对小麦赤霉的抑制率为65.3%; 化合物6f对花生褐斑的抑制率为67.3%; 化合物6g对苹果轮纹的抑制率为56.1%.

关键词： 酰基脲; 噻唑; 合成; 生物活性

本文引用格式

戴红 , 赵元飞 , 牛平 , 钱翊钧 , 李永强 , 方建新 , 石玉军 . 1-{4-[(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-噻唑-2-基}-3-取代苯甲酰基脲类化合物的合成及其生物活性[J]. 有机化学, 2013 , 33(07) : 1568 -1572 . DOI: 10.6023/cjoc201301068

Abstract

In search of novel thiazole derivatives with potent biological activities, a series of new thiazole compounds 6 containing acyl urea moiety were synthesized by the condensation of 2-cyanoimino-3-(2-aminothiazol-4-ylmethyl)thiazolidine with various arylacylisocyanates. The structures of the target compounds were determined by 1H NMR, MS and elemental analysis. The structures of 6a, 6e and 6h were further characterized by 13C NMR spectra. The bioassay data indicated that some of the title compounds showed fungicidal activities to some extent at the concentration of 50 μg/mL. For example, compound 6d displayed 65.3% inhibition rate against Gibberella zeae, compound 6f exhibited 67.3% inhibition rate against Cercospora arachidicola, and compound 6g showed 56.1% inhibition rate against Physalospora piricola.

Key words： acyl urea; thiazole; synthesis; biological activity

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