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Chinese Journal of Organic Chemistry >

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

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

Articles

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
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  • 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).

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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

Cite this article

Zhang Jiwei , Li Yongqiang , Yang Xinling , Chen Lulu , Miao Hongjian , Li Hui , Wang Xianwei , Ling Yun . Synthesis and Bioactivities of Nucleoside Compounds Containing Substituted Benzoyl Carbamate Thiourea[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 305 -311 . DOI: 10.6023/cjoc201210036

References

[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.
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