Citation: Wang Yan-Jiao, Zhou Da-Gui, He Fang-Cheng, Chen Ji-Xiang, Chen Yong-Zhong, Gan Xiu-Hai, Hu De-Yu, Song Bao-An. Synthesis and antiviral bioactivity of novel chalcone derivatives containing purine moiety[J]. Chinese Chemical Letters, ;2018, 29(1): 127-130. doi: 10.1016/j.cclet.2017.07.006 shu

Synthesis and antiviral bioactivity of novel chalcone derivatives containing purine moiety

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China

Corresponding author: Hu De-Yu, dyhu@gzu.eud.cn Song Bao-An, basong@gzu.edu.cn
Received Date: 9 April 2017
Revised Date: 17 May 2017
Accepted Date: 5 July 2017
Available Online: 13 January 2017

Figures(2)

A series of novel chalcone derivatives containing purine moiety was designed and synthesized, and their antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) were evaluated in vivo. Bioactivity assays indicated that some compounds showed good antiviral activities against CMV and TMV. It is worth mentioning that compounds 3o, 3s, 3w, and 3x exhibited excellent curative activity against CMV, with EC₅₀ values of 301.1 μg/mL, 315.7 μg/mL, 282.3 μg/mL, 230.5 μg/mL, respectively, which were better than that of Dufulin (373.7 μg/mL) and Ribavirin (726.3 μg/mL). In addition, the fluorescence spectroscopy experiment results showed that compound 3o showed strong combining capacity to tobacco mosaic virus coat protein.
- Chalcone derivatives,
- 6-Chloro-purine,
- Antiviral activity,
- Cucumber mosaic virus,
- Tobacco mosaic virus,
- Interaction mechanisms
1. [1]
  D.R. An, Chin. Bull. Life Sci. 2(1994) 15-18.
2. [2]
  L. H. Xie, Q. Y. Lin, Z. J. Wu, Plant Virus, 2th. ed., Science Press Beijing, 2009.
3. [3]
  G.P. Zhang, G.F. Hao, J.K. Pan, et al., J. Agric. Food. Chem. 64(2016) 4207-4213. doi: 10.1021/acs.jafc.6b01256
4. [4]
  X.H. Gan, D.Y. Hu, P. Li, et al., Pest Manag. Sci. 72(2015) 534-543.
5. [5]
  S. Zhang, X.Y. Liu, Prog. Pharm. Sci. 36(2012) 241-251.
6. [6]
  H. Jin, Y.C. Geng, Z.Y. Yu, et al., Pestic. Biochem. Physiol. 93(2009) 133-137. doi: 10.1016/j.pestbp.2009.01.002
7. [7]
  V.R. Solomon, H. Lee, Biomed. Pharmacother. 66(2012) 213-220. doi: 10.1016/j.biopha.2011.11.013
8. [8]
  H. Xu, X.M. Wang, X. Wei, et al., Chin. Chem. Lett. 20(2009) 576-578. doi: 10.1016/j.cclet.2009.01.013
9. [9]
  B.T. Yin, C.Y. Yan, X.M. Peng, et al., Eur. J. Med. Chem. 71(2014) 148-159. doi: 10.1016/j.ejmech.2013.11.003
10. [10]
  R. Kumar, P. Sharma, A. Shard, et al., Med. Chem. Res. 21(2012) 922-931. doi: 10.1007/s00044-011-9602-8
11. [11]
  G. Pasquale, G.P. Romanelli, J.C. Autino, et al., J. Agric. Food. Chem. 60(2012) 692-697. doi: 10.1021/jf203374r
12. [12]
  G. Du, J.M. Han, W.S. Kong, et al., Bull. Korean Chem. Soc. 34(2013) 1263-1265. doi: 10.5012/bkcs.2013.34.4.1263
13. [13]
  Z.Y. Liang, X.S. Yang, Y. Wang, et al., Chin. Chem. Lett. 21(2010) 818-820. doi: 10.1016/j.cclet.2010.03.021
14. [14]
  Y.W. Zhang, For. Med. Sci. Sect. Pharm. 23(1996) 218-223.
15. [15]
  Z.W. Chen, P. Li, B.A. Song, et al., Arab. J. Chem. (2015), doi:http://dx.doi.org/10.1016/j.arabjc.2015.05.003. doi: 10.1016/j.arabjc.2015.05.003
16. [16]
  M.H. Chen, P. Li, D.Y. Hu, et al., Bioorg. Med. Chem. Lett. 26(2016) 168-173. doi: 10.1016/j.bmcl.2015.11.006
17. [17]
  Z.H. Wan, D.Y. Hu, P. Li, et al., Molecules 20(2015) 11861-11874. doi: 10.3390/molecules200711861
18. [18]
  X.Z. Fu, F.J. Jiang, Y. Ou, et al., Chin. Chem. Lett. 25(2014) 115-118. doi: 10.1016/j.cclet.2013.09.013
19. [19]
  J. P. Verheyden, J. C. Martin, Patent, US 4355032 A, 1982, CAN 98: 53544.
20. [20]
  S. M. Daluge, Patent, EP 434450 A2, 1998, CAN 115: 208462.
21. [21]
  S. Antebi, B. Z. Dolitzky, D. Ioffe, et al. Patent, WO 2005026167 A1, 2005, CAN 142: 316618.
22. [22]
  A. Conejo-García, M.E. García-Rubiño, J.A. Marchal, et al., Eur. J. Med. Chem. 46(2011) 3795-3801. doi: 10.1016/j.ejmech.2011.05.046
23. [23]
  S.B. Wang, X.Q. Deng, D.C. Liu, et al., Med. Chem. Res. 23(2014) 4619-4626. doi: 10.1007/s00044-014-1030-0
24. [24]
  S. Kinali-Demirci, Ö. Idil, A. Di _şli, Med. Chem. Res. 24(2015) 1218-1225. doi: 10.1007/s00044-014-1209-4
25. [25]
  H. P. Hu, Synthesis and bioactivity of APP-like derivatives containing purine group, Central China Normal University, 2009 Master dissertation.
26. [26]
  D.Y. Zhao, M. Li, J.L. Yu, et al., Agrochemicals 39(2000) 36-39.
27. [27]
  F. Wu, P. Li, D.Y. Hu, et al., Res. Chem. Intermed. 42(2016) 7153-7168. doi: 10.1007/s11164-016-2524-9
28. [28]
  B. Nijampatnam, L. Casals, R.W. Zheng, et al., Bioorg. Med. Chem. Lett. 26(2016) 3508-3513. doi: 10.1016/j.bmcl.2016.06.033
29. [29]
  G.D. Celik, A. Disli, Y. Oner, et al., Med. Chem. Res. 22(2013) 1470-1479. doi: 10.1007/s00044-012-0140-9
30. [30]
  B.A. Song, H.P. Zhang, H. Wang, et al., J. Agric. Food Chem. 53(2005) 7886-7891. doi: 10.1021/jf051050w
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