Photophysical evaluation on the electronic properties of synthesized biologically significant pyrido fused imidazo[4,5-c]quinolines

A single pot microwave assisted method was employed to synthesize a series of novel pyrido fused imidazo[4,5-c]quinolines. The electronic properties of these derivatives were investigated by following their photophysical behaviour under isolated and solvated conditions via computational and experimental approaches. The solvatochromic effect of these derivatives was investigated in the ground and excited singlet states by following the absorption and fluorescence emission and excitation spectra. Further the effect of general and specific solvent effects were also investigated by plotting Stokes shift against Lippert-Mataga, ET(30) and Kamlet-Taft polarity parameters respectively. The deviation from linearity in ET(30) plot indicates that formation of different species in polar protic solvents. The biological applications of these derivatives as potential drug candidates were evaluated by in silico computational methods followed by pharmacokinetic properties predictions. The ability of these derivatives to inhibit human casein kinase 2 (CK2) was evaluated. The structure activity relationships were correlated by evaluating the electronic properties through experimental photophysical investigations including solvatochromic effect and computational electronic structure calculations. Of the various derivatives, p-nitro phenyl substituted pyrido fused imidazo[4,5-c]quinoline exhibited good inhibitory activity against CK2 enzyme and hence could serve as a promising drug candidate.

Automated summary

A microwave assisted method was used to synthesize novel pyrido fused imidazo[4,5-c]quinolines. The electronic properties of these compounds were investigated using computational and experimental methods. The solvatochromic effect and solvent effects were studied, and the potential inhibitory activity of these compounds against human casein kinase 2 (CK2) was evaluated. Among the derivatives, the p-nitro phenyl substituted pyrido fused imidazo[4,5-c]quinoline showed promising inhibitory activity against CK2 and could be a potential drug candidate.