Citation: Huang Fangfang, Ling Huan, Li Jiao, Lu Sen, Liu Weijie, Li Qingshan, Xu Fengbo. Synthesis, bioactivities and 3D-QSAR of novel avermectin B_2a aglycon derivatives[J]. Chinese Chemical Letters, ;2020, 31(1): 141-144. doi: 10.1016/j.cclet.2019.03.054 shu

Synthesis, bioactivities and 3D-QSAR of novel avermectin B_2a aglycon derivatives

State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

qli@nankai.edu.cn

xufb@nankai.edu.cn

Received Date: 10 March 2019
Revised Date: 27 March 2019
Accepted Date: 28 March 2019
Available Online: 29 January 2019

Figures(4)

Fourteen avermectin B_2a aglycon derivatives were designed and synthesized after removing the oleandrose disaccharide of avermectin B_2a. Their structures were characterized by ¹H NMR, ¹³C NMR, HMRS. Preliminary bioassays indicated that these compounds exhibited good insecticidal activity against diamondback moth at 200 mg/L, with mortality no less than 90%. Compounds 10b, 12a, 12c, 17 demonstrated good acaricidal activity against the adult mites, larvae, and good inhibition rate of hatching to mite eggs of Tetranychus cinnabarinus. Compounds 5, 10b, 10c exhibited excellent fungicidal activity against fourteen fungal pathogens in vitro. 3D-QSAR analysis showed that the fungicidal activity of avermectin B_2a aglycon derivatives would be increased when a negatively charged and bulky group was introduced at 13-position, which will be instructive for the further modification of avermectin B_2a aglycon.
- Avermectin B_2a aglycon,
- Biological activity,
- Insecticide,
- Acaricide,
- Fungicide,
- 3D-QSAR
1. [1]
  G.S. Sun, J.J. Zhang, S.H. Jin, J.J. Zhang, RSC Adv. 8(2018) 3774-3781. doi: 10.1039/C7RA13258A
2. [2]
  Q.A. Wu, Z.Y. Xu, M. Zheng, et al., Chin. Chem. Lett. 15(2004) 765-767.
3. [3]
  S.S. Pong, C.C. Wang, L.C. Fritz, J. Neurochem. 34(2010) 351-358.
4. [4]
  W.L. Shoop, H. Mrozik, M.H. Fisher, Vet. Parasitol. 59(1995) 139. doi: 10.1016/0304-4017(94)00743-V
5. [5]
  Y.M. Jia, X.M. Liang, X.Q. Fang, et al., Chin. Chem. Lett. 18(2007) 895-898. doi: 10.1016/j.cclet.2007.06.003
6. [6]
  P. Sun, Q.F. Zhao, F.T. Yu, et al., J. Am. Chem. Soc. 135(2013) 1540-1548. doi: 10.1021/ja311339u
7. [7]
  J. Zhang, X. Nan, H.T. Yu, et al., Eur. J. Med. Chem. 121(2016) 422-432. doi: 10.1016/j.ejmech.2016.05.056
8. [8]
  W.C. Campbell, Curr. Pharm. Biotechnol. 13(2012) 853-865. doi: 10.2174/138920112800399095
9. [9]
  M.H. Fisher, ACS Symp. Ser. 524(1993) 169.
10. [10]
  H. Mrozik, P. Eskola, M.H. Fisher, et al., J. Med. Chem. 25(1982) 658-663. doi: 10.1021/jm00348a010
11. [11]
  R. Prichard, C. Ménez, A. Lespine, Int. J. Parasitol: Drugs Drug Resist. 2(2012) 134-153. doi: 10.1016/j.ijpddr.2012.04.001
12. [12]
  A.P. Liu, J.R. Yao, Agrochem. 43(2004) 196-200.
13. [13]
  H. Mrozik, P. Eskola, B.H. Arison, J. Org. Chem. 47(1982) 489-492. doi: 10.1021/jo00342a023
14. [14]
  J.H. Song, Synthesis and Bioactivity Study and SAR of Natural Product Harmaline and Harmine and their Derivatives, Doctoral Dissertation, Nankai University, 2014.
15. [15]
  E.R. Collantes, W. Tong, W.J. Weish, W.L. Zielinski, Anal. Chem. 68(1996) 2038-2043. doi: 10.1021/ac951116u
16. [16]
  E.R. Collantes, L. Xing, P.C. Miller, W.J. Welsh, S. Profeta, J. Agric. Food Chem. 47(1999) 5245-5251. doi: 10.1021/jf9903410
17. [17]
  M.Z. Wang, L. Zhang, X.W. Wang, et al., Chin. Chem. Lett. 29(2018) 1375-1378. doi: 10.1016/j.cclet.2017.11.022
18. [18]
  B.L. Wang, Y.X. Shi, Y. Ma, J. Agric. Food Chem. 58(2010) 5515-5522. doi: 10.1021/jf100300a
19. [19]
  J.X. Chen, X.H. Gan, C.F. Yi, et al., Chin. J. Chem. 36(2018) 939-944. doi: 10.1002/cjoc.201800282
20. [20]
  X.J. Zou, L.H. Lai, G.Y. Jin, Z.X. Zhang, J. Agric. Food Chem. 50(2002) 3757-3760. doi: 10.1021/jf0201677
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2. [2]
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沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis, bioactivities and 3D-QSAR of novel avermectin B2a aglycon derivatives

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通讯作者: 陈斌, bchen63@163.com

Synthesis, bioactivities and 3D-QSAR of novel avermectin B_2a aglycon derivatives