Citation: Li Kejian, Wu Shuangzhi, Wang Nannan, Zhu Xiaolei, Yang Guangfu. Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2978-2984. doi: 10.6023/cjoc201706029 shu

Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors

Li Kejian ^a,b ,
Wu Shuangzhi ^a ,
Wang Nannan ^a ,
Zhu Xiaolei ^a,, ,
Yang Guangfu ^a,,

a.
Key Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079
b.
Department of Public Security, Sichuan Police College, Luzhou, Sichuan 646000

Corresponding author: Zhu Xiaolei, xlzhu@mail.ccnu.edu.cn Yang Guangfu, gfyang@mail.ccnu.edu.cn
Received Date: 21 June 2017
Revised Date: 10 July 2017
Available Online: 18 November 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21472065), the 111 Project (No. B17019) and the Fundamental Research Funds for the Central Universities (No. CCNU15A02013)

Figures(3)

Acetyl-CoA carboxylase (ACCase, EC 6.4.1.2) was one of important herbicidal targets. However, the number of resistant weeds targeting to ACCase had risen to the third place among all of herbicidal targets. Therefore, it is of great importance to design new ACCase inhibitors. Herein, based on the crystal structures, aryloxyphenoxypropanotes (APP)-site and cyclohexanedioneoximes (CHD)-site were used to constructing APP+CHD-site, and then thirteen compounds were designed and synthesized. All the newly prepared compounds were characterized by ¹H NMR, ¹³C NMR and HRMS. The molecular docking showed that 2-((4-(2, 4-dichlorophenoxy)phenoxy)methyl)-5-(2-(ethylthio)propyl)cyclohexane-1, 3-dione (10a) could occupy not only APP-site, but also CHD-site. In addition, based on the herbicidal activity, some compounds showed some inhibition rate upon tested weeds. Most importantly, 5-(2-(ethylthio)propyl)-2-((4-phenoxyphenoxy)methyl)cyclohexane-1, 3-dione (10b) showed a wide range of herbicidal spectrum, which could be used to inhibit not only poaceae weeds, but also broadleaf weeds. All these results indicated that this type of compounds worth of the further investigation.
- ACCase,
- molecular docking,
- organic synthesis,
- herbicidal activity
1. [1]
  Prado, R.; Gonzdez-Gutierrez, J.; Menendez, J. Weed Sci. 2000, 48, 311. doi: 10.1614/0043-1745(2000)048[0311:RTACCI]2.0.CO;2
2. [2]
  Burton, J. D.; Gronwald, J. W.; Somers, D. A.; Connelly, J. A.; Gengenbach, B. G.; Wyse, D. L. Biochem. Biophys. Res. Commun. 1987, 148, 1039. doi: 10.1016/S0006-291X(87)80236-X
3. [3]
  Babczinski, P.; Fischer, R. Pestic. Sci. 1991, 33, 455. doi: 10.1002/ps.v33:4
4. [4]
  Matthews, N.; Powles, S. B.; Preston, C. Pest Manage. Sci. 2000, 56, 441. doi: 10.1002/(ISSN)1526-4998
5. [5]
  Burton, J. D.; Gronwald, J. W.; Keith, R. A. Pestic. Biochem. Physiol. 1991, 39, 100. doi: 10.1016/0048-3575(91)90130-E
6. [6]
  Itomaso, J. M.; Brown, P. H.; Stowe, A. E. Plant Physiol. 1991, 95, 1063. doi: 10.1104/pp.95.4.1063
7. [7]
  Nikolau, B. J.; Ohlrogge J. B.; Wurtele, E. S. Arch. Biochem. Biophys. 2003, 414, 211. doi: 10.1016/S0003-9861(03)00156-5
8. [8]
  Mohamed, I. A.; Li, R. Z.; You, Z. G. Weed Sci. 2012, 60, 167. doi: 10.1614/WS-D-11-00111.1
9. [9]
  Han, J. T.; Wang, J. M.; Dong, H. B.; Xu, Z. H.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2013, 33, 596(in Chinese).
10. [10]
  Xu, Z. H.; Dong, H. B.; Liu, B.; Kong, L. Q.; Wang, M. A. Chin. J. Org. Chem. 2015, 35, 411(in Chinese).
11. [11]
  Sandra, L.; Joachim, J.; Guido, M.; Michael, K.; Thomas, S.; Bernd, W. WO 200 610 474, 2006[Chem. Abstr. 2006, 103516].
12. [12]
  Coret, J. M. US 7329770, 2005[Chem. Abstr. 2005, 1335545].
13. [13]
  Becker, W.; Langeluddeeke, P.; Leditschke, H. US 3954442, 1974[Chem. Abstr. 1974, 70543].
14. [14]
  Loehnert, G.; Hansigk, H. D. DE 2327954, 1975[Chem. Abstr. 1975, 125068].
15. [15]
  Xu, Z. H.; Zhang, T.; Wang, S. K.; Li, J. K. Chin. J. Org. Chem. 2017, 37, 526(in Chinese).
16. [16]
  Tatao, L.; William, L. GB 2179352, 1987[Chem. Abstr. 1987, 213492].
17. [17]
  Graham, J. B.; Lindsay, E. C.; Graeme, J. F.; Wendy, A. J.; Jack, L.; Alexander, S.; Richard, B. W. and Keith, G. W. Bioorg. Med. Chem. Lett. 1997, 12, 1489.
18. [18]
  Kim, D. S.; Chun, S. J.; Jeon, J. J.; Lee, S. W.; Joe, G. H. Pest Manage. Sci. 2004, 60, 1007. doi: 10.1002/(ISSN)1526-4998
19. [19]
  John, W.; Sandra, J.; Allan, R. US 6300281, 2001[Chem. Abstr. 2001, 741533].
20. [20]
  Prem, N. M.; Michael, P.; Sammes. J. Chem. Soc., Perkin. Trans. 1988, pp. 161~168.
21. [21]
  Tsutomu, K.; Kiyoshi, K.; Mikio, S. US 4355184, 1982[Chem. Abstr. 1982, 103658].
22. [22]
  Bernard, L. Synth. Commun. 1992, 22, 2343. doi: 10.1080/00397919208019089
23. [23]
  Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Comput. Chem. 1998, 19, 1639. doi: 10.1002/(ISSN)1096-987X
24. [24]
  Xiong, L.; Li, H.; Jiang, L. N.; Ge, J. M.; Yang, W. C.; Zhu, X. L.; Yang, G. F. J. Agric. Food Chem. 2017, 65, 1021. doi: 10.1021/acs.jafc.6b05134
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