Catalyst-free one-pot three-component synthesis and in silico bioactivity of new 4-pyrazolyl pyrano[3,4-c] pyrrole derivatives
摘要
An unexpected route for the synthesis of pyrano [3,4-c] pyrrole derivatives has been reported via catalyst-free, three-component reaction of 1,3-dicarbonyl pyrazole, aromatic primary amines and fumaryl chloride. This novel cascade reaction sequence led to create two new rings and four new σ bonds containing two C–N, one C–C, and one C–O bond. The newly synthesized compounds were elucidated on the basis of their spectroscopic data (1H, 13C, 2D NMR, HRMS, IR) and additionally confirmed by single-crystal X-ray diffraction analysis. The molecular docking simulation was performed utilizing the AutoDock 4.2 program to predict the binding affinity of one derivative of the synthesized compounds to the target mitogen-activated protein kinase P38 (MAPK P38) and mitogen-activated protein kinase 14 (MAPK 14).
Graphical abstract