Synthesis and anti-cancer activity of 1,4-disubstituted imidazo[4,5-c]quinolines.

Abstract

The synthesis and anti-cancer activity evaluation of fused imidazoquinoline compounds is reported in this paper. Yb(OTf)3 has been utilized as a catalyst for the synthesis of 1,4-diaryl substituted imidazo[4,5-c]quinolines via a modified Pictet-Spengler approach. The desired imidazole ring was synthesized from imines using TosMIC (toluenesulfonylmethyl isocyanide) and subsequently functionalized at the C-4 position yielding an imidazoquinoline skeleton. Importantly, the final step was carried out without the aid of any prefunctionalization to obtain the resultant compounds in good yields. The synthesized compounds, when screened for anti-cancer activity, revealed the highest activity with 4-(2-bromophenyl)-1-phenyl-1H-imidazo[4,5-c]quinoline (IC50: 103.3 μM).

DOI: 10.1039/c5ob01650a

Statistics

01000200020162017
Citations per Year

245 Citations

Semantic Scholar estimates that this publication has 245 citations based on the available data.

See our FAQ for additional information.

Cite this paper

@article{Thigulla2016SynthesisAA, title={Synthesis and anti-cancer activity of 1,4-disubstituted imidazo[4,5-c]quinolines.}, author={Yadagiri Thigulla and Mahesh Akula and Prakruti Harshvardhanbhai Trivedi and Balaram Ghosh and Mukund Jha and Anupam Bhattacharya}, journal={Organic & biomolecular chemistry}, year={2016}, volume={14 3}, pages={876-83} }