Highly efficient construction of multi-substituted aminopyrazoles derivatives via iodine-mediated three-components reaction as potential anticancer agents
文献类型: 外文期刊
作者: Gao, Zilin 1 ; Huang, Wenbo 3 ; Liu, Manli 1 ; Chen, Yu 2 ; Shi, Liqiao 1 ; Zhang, Zhigang 1 ; Yang, Fei 1 ; Cao, Xiufang 2 ; Wang, Kaimei 1 ; Ke, Shaoyong 1 ;
作者机构: 1.Hubei Acad Agr Sci, Natl Biopesticide Engn Res Ctr, Hubei Biopesticide Engn Res Ctr, Key Lab Microbial Pesticides,Minist Agr & Rural A, Wuhan, Peoples R China
2.Huazhong Agr Univ, Coll Sci, Wuhan, Peoples R China
3.Hubei Three Gorges Lab, Yichang, Peoples R China
4.Wuhan Univ, Coll Life Sci, Wuhan, Peoples R China
5.Hubei Acad Agr Sci, Hubei Biopesticide Engn Res Ctr, Wuhan 430064, Peoples R China
关键词: Aminipyrazole derivatives; three-component reaction; reaction mechanism; biological application; SARs; kinase inhibitor; molecular docking
期刊名称:GREEN CHEMISTRY LETTERS AND REVIEWS ( 影响因子:6.6; 五年影响因子:6.0 )
ISSN: 1751-8253
年卷期: 2023 年 16 卷 1 期
页码:
收录情况: SCI
摘要: As an important class of natural products, pyrazole alkaloids have a large number of applications in various aspects such as medicines and pesticides. Due to the special position of its amino group, 3-aminopyrazole is easy to form a hydrogen bond donor-acceptor-donor, and the hydrogen bond 'zipper' structure enhances the binding ability of such compounds to receptors. This work provides a new one-pot three-components reaction for the efficient construction of multi-substituted aminopyrazoles derivatives via iodine-mediated cyclization in the presence of ethanol. After that, the potential mechanism of the reaction was explored based on the control transformation experimental and density functional theory (DFT) calculations. In addition, all obtained multi-substituted aminopyrazole derivatives were fully investigated for their application as potential anti-cancer agents, and some of which have been proved to exhibit excellent anti-cancer activity against A875 and HepG2 cell lines, and the possible structure-activity relationships also has been discussed based on the screening results. The kinase assay and molecular docking results indicate that these compounds may be potential CDK1 inhibitors. [GRAPHICS]
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