SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 02: 305 - 311

DOI: https://doi.org/10.6023/cjoc201210036

研究论文

含酰基氨基甲酸酯基硫脲核苷类化合物的合成及生物活性

  • 张继伟 ,
  • 李永强 ,
  • 杨新玲 ,
  • 陈路路 ,
  • 苗宏健 ,
  • 李慧 ,
  • 王献伟 ,
  • 凌云
展开
  • a 中国农业大学理学院应用化学系 农业部农药化学及应用重点开放实验室 北京 100193;
    b 南开大学元素有机化学国家重点实验室 天津 300071

收稿日期: 2012-10-24

  修回日期: 2012-11-16

  网络出版日期: 2012-11-23

基金资助

国家自然科学基金(No. 21072222);国家973计划(No. 2010CB126104)和“十二五”科技支撑计划(No. 2011BAE06B05-5)资助项目.

收起

Synthesis and Bioactivities of Nucleoside Compounds Containing Substituted Benzoyl Carbamate Thiourea

  • Zhang Jiwei ,
  • Li Yongqiang ,
  • Yang Xinling ,
  • Chen Lulu ,
  • Miao Hongjian ,
  • Li Hui ,
  • Wang Xianwei ,
  • Ling Yun
Expand
  • a Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
    b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received date: 2012-10-24

  Revised date: 2012-11-16

  Online published: 2012-11-23

Supported by

Project supported by the National Natural Science Fundation of China (No. 21072222), the National Basic Research Program of China (973 Program) (No. 2010CB126104), and the National “Twelfth Five-Year” Plan for Science & Technology Support (No. 2011BAE06B05-5).

Fold

摘要

在前期核苷类化合物的研究基础之上, 为了进一步改善该类化合物的生物活性, 基于几丁质合成酶催化作用机制, 通过活性亚结构拼接方法, 将具有良好生物活性的氨基甲酸酯基片段引入到前期所设计化合物的硫脲桥当中, 设计合成了一系列结构新颖的含酰基氨基甲酸酯基硫脲的核苷类化合物. 以尿苷为原料, 经4步反应制得目标物, 其结构经IR, 1H NMR及HRMS确证. 初步生测结果表明, 部分化合物具有一定的杀菌和杀虫活性, 化合物5j对棉铃虫的抑制活性与对照药剂除虫脲相当.

关键词： 几丁质; 尿苷; 氨基甲酸酯基硫脲; 合成; 生物活性

本文引用格式

张继伟 , 李永强 , 杨新玲 , 陈路路 , 苗宏健 , 李慧 , 王献伟 , 凌云 . 含酰基氨基甲酸酯基硫脲核苷类化合物的合成及生物活性[J]. 有机化学, 2013 , 33(02) : 305 -311 . DOI: 10.6023/cjoc201210036

Abstract

In order to find new fungicidal and insecticidal lead compounds, base on the catalytic mechanism of chitin synthase and our previous work, a series of novel nucleoside compounds containing carbamate thiourea group were designed via the method of linking active sub-structures, in which the carbamate group with good bioactivities was combined to the uridine part. The target compounds were synthesized from uridine in 4 steps. Their structures were confirmed by IR, 1H NMR and HRMS. The preliminary bioassay results indicated that some compounds showed moderate to good fungicidal and insecticidal activities. Compound 5j possessed comparable activity against Pyrausta nubilalis with the control diflubenzuron.

Key words： chitin; uridine; carbamate thiourea; synthesis; bioactivity

参考文献

[1] Ephraim, C. Pest Manage. Sci. 2001, 57, 946.

[2] Gooday, G. W. In The Biochemistry of Cell Walls and Membranes in Fungi, Eds.: Goosey, M.; Kuhn, P.; Trinci, A. P., Springer-Ver-g, Berlin, 1989, pp. 61～76.

[3] Grosscurt, A. C.; Tipker, J. Pestic. Biochem. Physiol. 1980, 13, 249.

[4] (a) Isono, K.; Nagatsu, J.; Kawashiwa, Y.; Suzuki, S. Agric. Biol. Chem. 1965, 29, 848.
(b) Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91, 7490.
(c) Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333.

[5] (a) Dähn, J.; Hagenmaier, H.; Höhner, H.; König, W. A.; Wolf, G.; Zähner, H. Arch. Microbiol. 1976, 107, 143.
(b) Hagenmaier, H.; Keckeisen, A.; Zähner, H.; König, W. A. Liebigs Ann. Chem. 1979, 10, 1494.
(c) König, W. A.; Hass, W.; Dehler, W.; Fiedler, H. P.; Zähner, H. Liebigs. Ann. Chem. 1980, 4, 622.

[6] Khare, R. K.; Becker, J. M.; Naider, F. R. J. Med. Chem. 1988, 31, 650.

[7] Ephraim, C. Pest Manage. Sci. 2001, 57, 946.

[8] Miao, H.-J.; Zhang, J.-W.; Yuan H.-Z.; Li, Y.; Xu, Y.; Li, H.; Yang, X.-L. Ling, Y. Chin. J. Org. Chem. 2012, 32, 915 (in Chinese). (苗宏健, 张继伟, 袁会珠, 李映, 徐焱, 李慧, 杨新玲, 凌云, 有机化学, 2012, 32, 915.)

[9] Li, Y.; Li, B.-J.; Ling, Y.; Miao, H.-J.; Yang, X.-L. J. Agric. Food Chem. 2010, 58, 3037.

[10] Wayne, C. F.; William, W. L.; David, W. H. J. Med. Chem. 1973, 16, 570.

[11] Chen, N.-C. Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, p. 161 (in Chinese). (陈年春, 农药生物测定技术, 北京农业大学出版社, 北京, 1991, p. 161.)

[12] Shang, J.; Sun, R.-F.; Li, Y.-Q.; Huang, R.-Q.; Bi, F.-C.; Wang, Q.-M. J. Agric. Food Chem. 2010, 58, 1834.

[13] Julia, M.; Susana, F.; Miguel, F.; Vicente, G. J. Org. Chem. 1998, 63, 8873.
Options
文章导航

/

〈 〉