Catalyst-free one-pot three-component synthesis and in silico bioactivity of new 4-pyrazolyl pyrano[3,4-c] pyrrole derivatives

Abstract

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