Abstract

Pyrazole scaffold is an important building block in many of the medicinally active new chemical entities. In the current work, synthesis of pyrazole conjugated tetrahydroquinoline derivatives has been achieved by treating 3-methyl-1-phenyl-1H-pyrazol-5-amine (1), 5,5-dimethylcyclohexane-1,3-dione (2), and benzaldehydes (3) at 80-85 oC for 60-90 min using glycerol as green reaction medium. The anticancer activity of the synthesized pyrazoleconjugates was carried out on breast cancer (MCF-7) and liver cancer (A549) cell lines. Two among the tested compounds showed potential inhibition on A549 cell lines. Further, molecular modeling studies have performed and the binding interactions with the target protein have been observed. Additionally, pharmacokinetic properties such as bioavailability, log P, total polar surface area and blood brain barrier (BBB) have been predicted using SwissADME tools to get insight into the further structural optimization.

Key words: 3-Methyl-1-phenyl-1H-pyrazol-5-amine; 5,5-dimethylcyclohexane-1,3-dione; one-pot reaction; glycerol; anticancer activity.