Citation: Xiao-Hui JI, Juan ZHAO, Jiu-Fu LU, Hong-Guang GE. Synthesis, Crystal and Biological Activity of 3-(2, 4-Difluorobenzyl)-5-(p-tolyl)-7-(trifluoromethyl)pyrazolo[1, 5-a]pyrimidin-2-amine[J]. Chinese Journal of Structural Chemistry, ;2020, 39(10): 1912-1917. doi: 10.14102/j.cnki.0254–5861.2011–2700 shu

Synthesis, Crystal and Biological Activity of 3-(2, 4-Difluorobenzyl)-5-(p-tolyl)-7-(trifluoromethyl)pyrazolo[1, 5-a]pyrimidin-2-amine

Shaanxi Key Laboratory of Catalysis, College of Chemical & Environment Science, Shaanxi University of Technology, Hanzhong 723001, China

Corresponding author: Jiu-Fu LU, jiufulu@163.com Hong-Guang GE, gehg@snut.edu.cn
Received Date: 13 December 2019
Accepted Date: 16 February 2020

Fund Project: the Project of Shaanxi Provincial Science and Technology Department 2020JM602the Project of Shaanxi Provincial Science and Technology Department 2019JM471the Team of Syngas Catalytic Conversion of Shaanxi University of Technology, the Youth National Natural Science Foundation of China 21373132the Team of Syngas Catalytic Conversion of Shaanxi University of Technology, the Youth National Natural Science Foundation of China 21603133the Key Project of Education Department of Shaanxi Province 18JS023the Project of Shaanxi University of technology SLGQD2017-14

Figures(4)

The title compound 3-(2, 4-difluorobenzyl)-5-(p-tolyl)-7-(trifluoromethyl)pyrazolo[1, 5-a]pyrimidin-2-amine (6) was synthesized by the condensation of 4, 4, 4-trifluoro-1-(p-tolyl)butane-1, 3-dione (5) with 4-(2, 4-difluorobenzyl)-1H-pyrazole-3, 5-diamine (4). The latter was prepared from 2, 4-difluorobenzaldehyde (1) and malononitrile through Knoevenagel condensation and NaBH₃CN reduction and then cyclisation with hydrazine hydrate. The crystal structure of the title compound was determined and its crystal belongs to the triclinic system, space group P\begin{document}$ \overline 1 $\end{document} with a = 5.4939(9), b = 10.6480(17), c = 16.508(3) Å, α = 93.226(2)°, β = 97.050(2)° and γ = 98.325(2)°. In addition, the compound possesses distinct effective inhibition on the proliferation of MKN45, HT-29 and K562 cell lines with IC₅₀ values of 5.57, 7.72 and 0.83 μM, respectively, displaying promising anticancer activity.
- pyrazolo[1, 5-a]pyrimidine,
- synthesis,
- X-ray diffraction,
- antitumor activity
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