Citation: Yang Huibin, Qi Huitang, Hao Zesheng, Shao Xusheng, Liu Tian, Yang Qing, Qian Xuhong. Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-D-hexosaminidase and chitinase[J]. Chinese Chemical Letters, ;2020, 31(5): 1271-1275. doi: 10.1016/j.cclet.2019.11.035 shu

Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-D-hexosaminidase and chitinase

Yang Huibin ^a,b,1 ,
Qi Huitang ^c,1 ,
Hao Zesheng ^b ,
Shao Xusheng ^a ,
Liu Tian ^c ,
Yang Qing ^c,*, ,
Qian Xuhong ^a,*,

a.
Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals Research and Development Co., Ltd., Shenyang 110021, China
c.
School of Bioengineering, Dalian University of Technology, Dalian 116024, China

qingyang@dlut.edu.cn

xhqian@ecust.edu.cn

Received Date: 8 October 2019
Revised Date: 18 November 2019
Accepted Date: 20 November 2019
Available Online: 21 November 2019

Figures(6)

Insect chitinase and N-acetyl-β-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R₁ at N3) and II (with substituted group R₁ at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R₁, demonstrated the best inhibitory activities against OfHex1 and OfChi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (K_i=1.5 μmol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (K_i=5.9 μmol/L). The differences in compounds' binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (K_i=1.9 μmol/L) and II-3d (K_i=4.1 μmol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors.
- N-acetyl-β-D-hexosaminidase,
- Chitinase,
- Inhibitor,
- Chitin,
- Structure-activity relationship,
- Thiazolylhydrazone derivatives,
- Molecular docking
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