Ch. Venkata Ramana Reddy, G. G. Reddy
Mar 1, 2020
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Quality indicators
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Chemistry Africa
Abstract
A series of 3-methyl-4-((1-methyl-1 H -indol-3-yl) methylene)isoxazol-5(4 H )-ones were prepared by one-pot three-component reaction of 1-methyl-1 H -indole-3-carbaldehyde with β-keto-esters and hydroxylamine hydrochloride in aqueous media. In an alternative method the same compounds were prepared by Knoevenagel condensation of 1-methyl-1 H -indole-3-carbaldehyde with isoxazolone in the presence of water and sodium benzoate as a catalyst under ultrasound irradiation. The advantages of these methods include green conditions, high yields, easy work-up procedures and shorter reaction times. The catalyst was found to remain active up to five reaction cycles and no substainal loss of activity was observed. All the synthesized compounds were docked against BCL-2 protein, an expressed protein of liver cancer. Compounds 6d , 6e , 6f , 6g , and 6l exhibited best docking interactions, which were further screened for their in vitro anti-cancer activity in HepG2 cell lines and IC 50 values ranging between 37 and 57 μg/mL.