Citation: Xuan-Qi Liu, Ya-Qin Liu, Xu-Sheng Shao, Zhi-Ping Xu, Xiao-Yong Xu, Zhong Li. Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives[J]. Chinese Chemical Letters, ;2016, 27(01): 7-10. doi: 10.1016/j.cclet.2015.10.002 shu

Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives

1.
a Shanghai Key Lab of Chemistry Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;
2.
b Shanghai Collaborative Innovation Center for Biomanufacturing Technology, Shanghai 200237, China

Corresponding author: Zhong Li,
Received Date: 6 May 2015
Available Online: 17 June 2015
Fund Project: This work was financial supported by National High Technology Research Development Program of China(863 Program, No. 2011AA10A207) (863 Program, No. 2011AA10A207) National Natural Science Foundation of China(Nos. 21472046, 21372079) (Nos. 21472046, 21372079) Shanghai Pujiang Program(No. 14PJD012) (No. 14PJD012)the Fundamental Research Funds for the Central Universities(No. 222201414015). This work was also partly supported by Australia DC Foundation. (No. 222201414015)

A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore(=CNO₂) were synthesized via practical aza-ene reaction and characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper(Nilaparvata lugens) and cowpea aphids(Aphis craccivora) at 500 mg L^-1. Among them, compound 11h was active against brown planthopper at 100 mg L^-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.
- Neonicotinoids,
- Tetrahydroimidazo[1,2-a]pyridin-5(1H)-,
- one,
- Configuration,
- Insecticidal activity
1. [1]
  [1] R. Nauen, U. Ebbinghaus-Kintscher, A. Elbert, P. Jeschke, K. Tietjen, Acetylcholine receptors as sites for developing neonicotinoid insecticides, in:I. Ishaaya(Ed.), Biochemical Sites of Insecticide Action and Resistance, Springer Berlin Heidelberg, Berlin, 2001, pp. 77-105.
2. [2]
  [2] P. Jeschke, R. Nauen, M.E. Beck, Nicotinic acetylcholine receptor agonists:a milestone for modern crop protection, Angew. Chem. Int. Ed. 52(2013) 9464-9485.
3. [3]
  [3] R. Nauen, I. Denholm, Resistance of insect pests to neonicotinoid insecticides:current status and future prospects, Arch. Insect Biochem. Physiol. 58(2005) 200-215.
4. [4]
  [4] N. Rauch, R. Nauen, Identification of biochemical markers linked to neonicotinoid cross resistance in Bemisia tabaci(Hemiptera:Aleyrodidae), Arch. Insect Biochem. Physiol. 54(2003) 165-176.
5. [5]
  [5] D. Mota-Sanchez, R.M. Hollingworth, E.J. Grafius, D.D. Moyer, Resistance and cross-resistance to neonicotinoid insecticides and spinosad in the Colorado potato beetle, Leptinotarsa decemlineata(Say)(Coleoptera:Chrysomelidae), Pest Manag. Sci. 62(2006) 30-37.
6. [6]
  [6] Y.F. Fan, W.W. Zhang, X.S. Shao, et al., Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives, Chin. Chem. Lett. 26(2015) 1-5.
7. [7]
  [7] N.Y. Chen, L.P. Ren, M.M. Zou, et al., Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs, Chin. Chem. Lett. 25(2014) 197-200.
8. [8]
  [8] K.L. Eley, L.M. Halo, Z.S. Song, et al., Biosynthesis of the 2-pyridone tenellin in the insect pathogenic fungus Beauveria bassiana, ChemBioChem 8(2007) 289-297.
9. [9]
  [9] K. Schmidt, W. Günther, S. Stoyanova, et al., Militarinone A, a neurotrophic pyridone alkaloid from Paecilomyces militaris, Org. Lett. 4(2002) 197-199.
10. [10]
  [10] K. Schmidt, U. Riese, Z.Z. Li, M. Hamburger, Novel tetramic acids and pyridone alkaloids, militarinones B, C, and D, from the insect pathogenic fungus Paecilomyces militaris, J. Nat. Prod. 66(2003) 378-383.
11. [11]
  [11] L.P. Ren, Y.P. Lou, N.Y. Chen, et al., Synthesis and insecticidal activities of tetrahydroimidazo[1,2-a]pyridinones:further exploration on cis-neonicotinoids, Synth. Commun. 44(2014) 858-867.
12. [12]
  [12] J. Alder, J. Clement, J. Meulbroek, N. Shipkowitz, et al., Efficacies of ABT-719 and related 2-pyridones, members of a new class of antibacterial agents, against experimental bacterial infections, Antimicrob. Agents Chemother. 39(1995) 971-975.
13. [13]
  [13] L.N. Yin, Q.Z. Hu, R.W. Hartmann, Tetrahydropyrroloquinolinone type dual inhibitors of aromatase/aldosterone synthase as a novel strategy for breast cancer patients with elevated cardiovascular risks, J. Med. Chem. 56(2013) 460-470.
14. [14]
  [14] T. Kawasuji, B.A. Johns, H. Yoshida, et al., Carbamoyl pyridone HIV-1 integrase inhibitors. 2. Bi-and tricyclic derivatives result in superior antiviral and pharmacokinetic profiles, J. Med. Chem. 56(2013) 1124-1135.
15. [15]
  [15] E. Muraglia, O. Kinzel, C. Gardelli, et al., Design and synthesis of bicyclic pyrimidinones as potent and orally bioavailable HIV-1 integrase inhibitors, J. Med. Chem. 51(2008) 861-874.
16. [16]
  [16] X.B. Chen, D.D. Zhu, X.Y. Wang, S.J. Yan, J. Lin, Cascade reaction synthesis of multisubstituted bicyclic pyridone derivatives, Tetrahedron 69(2013) 9224-9236.
17. [17]
  [17] M. Tomizawa, N.J. Zhang, K.A. Durkin, M.M. Olmstead, J.E. Casida, The neonicotinoid electronegative pharmacophore plays the crucial role in the high affinity and selectivity for the Drosophila nicotinic receptor:an anomaly for the nicotinoid cation-π interaction model, Biochemistry 42(2003) 7819-7827.
18. [18]
  [18] X.S. Shao, W.W. Zhang, Y.Q. Peng, et al., cis-Nitromethylene neonicotinoids as new nicotinic family:synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-α]pyridine, Bioorg. Med. Chem. Lett. 18(2008) 6513-6516.
19. [19]
  [19] X.S. Shao, H.Y. Lu, H.B. Bao, et al., The mode of action of a nitroconjugated neonicotinoid and the effects of target site mutation Y151S on its potency, Insect Biochem. Mol. Biol. 41(2011) 440-445.
20. [20]
  [20] X.S. Shao, Z. Li, X.H. Qian, X.Y. Xu, Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids:replacement of nitromethylene with nitroconjugated system, J. Agric. Food Chem. 57(2009) 951-957.
21. [21]
  [21] X.S. Shao, P.W. Lee, Z.W. Liu, et al., cis-Configuration:a new tactic/rationale for neonicotinoid molecular design, J. Agric. Food Chem. 59(2011) 2943-2949.
22. [22]
  [22] X.S. Shao, H. Fu, X.Y. Xu, et al., Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid:design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58(2010) 2696-2702.
23. [23]
  [23] K. Moriya, K. Shibuya, Y. Hattori, et al., 1-(6-Chloronicotinyl)-2-nitroimino-imidazolidines and related compounds as potential new insecticides, Biosci. Biotechnol. Biochem. 56(1992) 364-365.
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