Design, Synthesis, and Antifungal Activities of Novel 1H-Triazole Derivatives Based on the Structure of the Active Site of Fungal Lanosterol 14α-Demethylase (CYP51)

2007 ◽  
Vol 4 (7) ◽  
pp. 1472-1479 ◽  
Author(s):  
Qing-Jie Zhao ◽  
Hong-Gang Hu ◽  
Yao-Wu Li ◽  
Yan Song ◽  
Ling-Zhi Cai ◽  
...  
Keyword(s):  
Active Site ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives

scholarly journals Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5852
Author(s):  
Hui Bai ◽  
Xuelian Liu ◽  
Pengfei Chenzhang ◽  
Yumei Xiao ◽  
Bin Fu ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Binding Modes ◽  
Oxime Ether ◽  
Single Crystal Diffraction ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
Pyridine Moiety ◽  
New Compounds

A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives

2011 ◽  
Vol 46 (7) ◽  
pp. 3142-3148 ◽  
Author(s):  
Jianming Xu ◽  
Yongbing Cao ◽  
Jun Zhang ◽  
Shichong Yu ◽  
Yan Zou ◽  
...  
Keyword(s):  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives

scholarly journals Design, synthesis, and antifungal activities of novel triazole derivatives containing the benzyl group

2015 ◽  
pp. 1459
Author(s):  
Shichong Yu ◽  
Kehan Xu ◽  
Lei Huang ◽  
Zheng Xu ◽  
Yanwei Wang ◽  
...  
Keyword(s):  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives

Design, synthesis, antifungal evaluation, and molecular docking of novel 1,2,4-triazole derivatives containing oxime ether and cyclopropyl moieties as potential sterol demethylase inhibitors

2021 ◽  
Author(s):  
Sheng-Xin Sun ◽  
Jing-Hua Yan ◽  
Jiang-Tao Zuo ◽  
Xiao-Bin Wang ◽  
Min Chen ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Oxime Ether ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives

A series of novel triazole derivatives containing oxime ether and cyclopropyl moieties were designed and synthesized. Some compounds exhibited remarkable antifungal activities. The molecular docking of compound 5k with FgCYP51 was investigated.

Design, Synthesis and Antifungal Activity of Novel 1-(Adamantan-1-yl) ethanone Oxime Esters

2020 ◽  
Vol 17 (5) ◽  
pp. 526-532
Author(s):  
Si Liu ◽  
Li-Zhi Niu ◽  
Yan-Hua Shi ◽  
Fu-Xian Wan ◽  
Lin Jiang
Keyword(s):  
Antifungal Activity ◽  
Biological Activities ◽  
Lead Compound ◽  
Design Synthesis ◽  
Antifungal Activities

Background: Oxime compounds, including oxime ethers and oxime esters, possess various biological activities. Many oxime ethers have been widely used in the fields of pesticides and medicines. However, oxime ethers are rarely used in the field of pesticides. Methods: We chose the excellent fungicide pyrifenox as the lead compound, integrated pyridinyl, adamantyl and benzoyl moieties into one molecule, while also designed and synthesized ten 1- (adamantan-1-yl)ethanone oxime esters containing pyridinyl moiety. Moreover, we also evaluated their preliminary antifungal activities against S. sclerotiorum and B. cinerea. Results: The target compounds were characterized by NMR, IR and HRMS. The preliminary bioactivity test showed that they exhibited some antifungal activity to S. sclerotiorum and B. cinerea, and EC50 values were in the range of 14.16-32.97 and 27.60-52.82 μg/mL, respectively. Conclusion: Some target compounds such as 3d, 3e, 3h and 3i, exhibited moderate activities against S. sclerotiorum, with EC50 values of 14.16-18.18 μg/mL.

Sign in / Sign up

Export Citation Format

Share Document