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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 2: 725 - 733

DOI: https://doi.org/10.6023/cjoc202207038

Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline

  • Huan Xu ,
  • Hongfei Wu ,
  • Xiaoming Zhang ,
  • Xingxing Lu ,
  • Tengda Sun ,
  • Yue Qi ,
  • Yufan Lin ,
  • Xinling Yang ,
  • Li Zhang ,
  • Yun Ling
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  • Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
* Corresponding author. E-mail:

Received date: 2022-07-28

  Revised date: 2022-08-18

  Online published: 2022-10-10

Supported by

National Natural Science Foundation of China(22077137); National Natural Science Foundation of China(21472236)

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Abstract

In order to find agricultural fungicide candidates with lassase as potential target, 14 unreported sulfonyl hydrazide and 9 hydrazide derivatives were designed and synthesized by replacing tetrahydroquinoline skeleton of the lead compound 4-methyl-N'-(1,2,3,4-tetrahydroquinoline-1-carbonothioyl)benzenesulfonohydrazide (4bg) with active fragment 1,2,3,4-tetra- hydro-isoquinoline. The structures of the target compounds were confirmed by 1H NMR, 13C NMR and HRMS. The in vitro bioassay showed that 2-methyl-N'-(1,2,3,4-tetrahydroisoquinoline-2-carbonothioyl)benzenesulfonohydrazide (4b) showed excellent fungicidal activity against V. Mali and S. sclerotiorum with EC50 values of 4.81 and 1.57 μg/mL, respectively, which were better than that of lead compound 4bg. In addition, 5-methyl-N'-(1,2,3,4-tetrahydroisoquinoline-2-carbonothioyl)pyra- zine-2-carbohydrazide (5i) showed good broad-spectrum fungicidal activity against V. Mali, S. sclerotiorum, B. cinerea, M. oryzae and F. graminearum with EC50 range of 12.88~28.65 μg/mL. Moreover, compounds 4b and 5i exhibited moderate laccase inhibitory activity (37.07%, 35.49%), which were similar to that of cysteine (43.10%) at 50 μg/mL. Furthermore, the binding modes of compounds 4b and 5i with laccase protein were simulated by molecular docking method, which provided guidance for further modification of compounds.

Key words： laccase inhibitor; 1,2,3,4-tetrahydroisoquinoline; (sulfonyl) hydrazide; fungicidal activity; molecular docking

Cite this article

Huan Xu , Hongfei Wu , Xiaoming Zhang , Xingxing Lu , Tengda Sun , Yue Qi , Yufan Lin , Xinling Yang , Li Zhang , Yun Ling . Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline[J]. Chinese Journal of Organic Chemistry, 2023 , 43(2) : 725 -733 . DOI: 10.6023/cjoc202207038

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