Citation: Zhang Xiao-Xiao, Jin Hong, Deng Yuan-Jie, Gao Xu-Heng, Li Yong, Zhao Yong-Tian, Tao Ke, Hou Tai-Ping. Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modified scaffold as potent antifungal agents[J]. Chinese Chemical Letters, ;2017, 28(8): 1731-1736. doi: 10.1016/j.cclet.2017.04.021 shu

Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modified scaffold as potent antifungal agents

Zhang Xiao-Xiao ^a,1 ,
Jin Hong ^a,1,, ,
Deng Yuan-Jie ^a ,
Gao Xu-Heng ^a ,
Li Yong ^b ,
Zhao Yong-Tian ^a ,
Tao Ke ^a ,
Hou Tai-Ping ^a,,

a.
Key Laboratory of Bio-Resource and Eco-environment of Ministry of Education, College of Life Sciences, Sichuan University, Chengdu 610064, China
b.
College of Chemistry, Sichuan University, Chengdu 610064, China

Corresponding author: Jin Hong, jinhong@scu.edu.cn Hou Tai-Ping, houtplab@scu.edu.cn

Received Date: 8 January 2017
Revised Date: 15 March 2017
Accepted Date: 30 March 2017
Available Online: 27 August 2017

Figures(7)

Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed, synthesized and characterized in detail via ¹H NMR, ¹³C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC₅₀ values of 0.013, 1.608 and 1.874 μg/mL, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC₅₀ value of 22.21 μg/mL. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.
- Pyrazole carboxamide,
- Synthesis,
- Antifungal activities,
- Diarylamine
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