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

• 作者: GE Hong-Guang JI Xiao-Hui LU Jiu-Fu ZHAO Juan
• 来源期刊: 结构化学
• 年，卷（期）: 2020,（10）
• 所属期刊栏目: medicinal structural chemistry
• 页码范围: 1912-1917
• 页数: 6页
• 语种: 英文
• DOI: 10.14102/j.cnki.0254-5861.2011-2700

摘要

The title compound 3-(2,4-difluorobenzyl)-5-(p-tolyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin2-amine (6) was synthesized by the condensation of 4,4,4-trifluoro-l-(p-tolyl)butane-l,3-dione (5) with 4-(2,4-difluorobenzyl)-lH-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(1) with a =5.4939(9),b =10.6480(17),c =16.508(3) (A),α =93.226(2)°,fβ =97.050(2)° and y =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.