Citation: Xi-Le Deng, Li Zhang, Xue-Ping Hu, Bin Yin, Pei Liang, Xin-Ling Yang. Target-based design, synthesis and biological activity of new pyrazole amide derivatives[J]. Chinese Chemical Letters, ;2016, 27(02): 251-255. doi: 10.1016/j.cclet.2015.10.006 shu

Target-based design, synthesis and biological activity of new pyrazole amide derivatives

Xi-Le Deng ^a ,
Li Zhang ^a,, ,
Xue-Ping Hu ^a ,
Bin Yin ^a ,
Pei Liang ^b ,
Xin-Ling Yang ^a,,

a.
a. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China;
b.
b. Department of Entomology, College of Agriculture and Biotechnology, China Agricultural University, Beijing 100193, China

Corresponding author: Li Zhang, Xin-Ling Yang,
Received Date: 23 June 2015
Available Online: 19 July 2015
Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21272265) (No. 21272265)

Based on the similarities in the conformation of VS008 (N-(4-methylphenyl)-3-(tert-butyl)-1-(phenylmethyl)-1H-pyrazole-5-carboxamide) and BYIO6830 (N'-(3,5-dimethylbenzoyl)-N'-tert-butyl-5-methyl-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide) bound to the active site of the EcR subunit of the ecdysone receptor (EcR)-ultraspiracle protein (USP) heterodimeric receptor, a series of new pyrazole amide derivatives were designed and synthesized. Their structures were confirmed by IR, ¹H NMR, ¹³C NMR and elemental analysis. Results from a preliminary bioassay revealed that two of the pyrazole derivatives exhibited promising insecticidal activity. Specifically, compounds 6e and 6i exhibited good activity against Helicoverpa armigera (cotton bollworm) at low concentration. Symptoms displayed by tebufenozide-treated H. armigera were identical with those displayed by its treated counterpart. 6i showed the same poisoning symptoms as those of tebufenozide. In addition, results from molecular docking result indicated that the binding modes of 6e and 6i at the active site of the EcR subunit of the heterodimeric receptor were similar to that of the bound tebufenozide.
- Molting hormone,
- Pyrazole amide,
- Rational design,
- Bioactivity,
- Molecular docking
1. [1]
  [1] Y. Nakagawa, V.C. Henrich, Arthropod nuclear receptors and their role in molting, FEBS J. 276 (2009) 6128-6157.
2. [2]
  [2] L.I. Gilbert, Halloween genes encode P450 enzymes that mediate steroid hormone biosynthesis in Drosophila melanogaster, Mol. Cell. Endocrinol. 215 (2004) 1-10.
3. [3]
  [3] R.J. Hill, I.M.L. Billas, F. Bonneton, L.D. Graham, M.C. Lawrence, Ecdysone receptors: from the Ashburner model to structural biology, Annu. Rev. Entomol. 58 (2013) 251-271.
4. [4]
  [4] K.D. Wing, RH-5849, a nonsteroidal ecdysone agonist: effects on a drosophila cell line, Science 241 (1988) 467-469.
5. [5]
  [5] T.S. Dhadialla, R.K. Jansson, Non-steroidal ecdysone agonists: new tools for IPM and insect resistance management, Pestic. Sci. 55 (1999) 357-359.
6. [6]
  [6] G.R. Carlson, T.S. Dhadialla, R. Hunter, et al., The chemical and biological properties of methoxyfenozide, a new insecticidal ecdysteroid agonist, Pest Manag. Sci. 57 (2001) 115-119.
7. [7]
  [7] Y. Sawada, T. Yanai, H. Nakagawa, et al., Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: part 2. Introduction of substituents on the benzene rings of the benzoheterocycle moiety, Pest Manag. Sci. 59 (2003) 36-48.
8. [8]
  [8] G. Holmwood, M. Schindler, Protein structure based rational design of ecdysone agonists, Bioorg. Med. Chem. 17 (2009) 4064-4070.
9. [9]
  [9] T. Harada, Y. Nakagawa, T. Ogura, et al., Virtual screening for ligands of the insect molting hormone receptor, J. Chem. Inf. Model. 51 (2011) 296-305.
10. [10]
  [10] Y. Bin, Design, Synthesis and Bioactivity of Novel IGRs Lead Compound Based on EcR/USP Structure, (Master dissertation), China Agricultural University, Beijing, 2011.
11. [11]
  [11] Y.F. Sun, H.L. Qiao, Y. Ling, et al., New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins, J. Agric. Food Chem. 59 (2011) 2456-2461.
12. [12]
  [12] W.L. Dong, J.Y. Xu, L.X. Xiong, X.H. Liu, Z.M. Li, Synthesis, structure and biological activities of some novel anthranilic acid esters containing N-pyridylpyrazole, Chin. J. Org. Chem. 27 (2009) 579-586.
13. [13]
  [13] J.W. Zhang, Y.Q. Li, X.L. Yang, et al., Synthesis and bioactivities of nucleoside compounds containing substituted benzoyl carbamate thiourea, Chin. J. Org. Chem. 33 (2013) 305-311.
14. [14]
  [14] X. Liu, L. Zhang, J.G. Tan, H.H. Xu, Design and synthesis of N-alkyl-N'-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist, Bioorg. Med. Chem. 21 (2013) 4687-4697.
15. [15]
  [15] Molecular Operating Environment (MOE), 2013.08; Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2013.
16. [16]
  [16] D.A. Case, T.A. Darden, T.E. Cheatham Ⅲ, et al., AMBER 12, University of California, San Francisco, 2012.
17. [17]
  [17] M. Tohnishi, H. Nakao, T. Furuya, et al., Flubendiamide, a novel insecticide highly active against lepidopterous insect pests, J. Pestic. Sci. 30 (2005) 354-360.
18. [18]
  [18] R. Nauen, Insecticide mode of action: return of the ryanodine receptor, Pest Manag. Sci. 62 (2006) 690-692.
19. [19]
  [19] G. Smagghe, D. Degheele, Action of a novel nonsteroidal ecdysteroid mimic, tebufenozide (Rh-5992), on insects of different orders, Pestic. Sci. 42 (1994) 85-92.
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