Anticancer Indole-Based Chalcones: A Structural and Theoretical Analysis

Abstract

The crystal structures of five new chalcones derived from N-ethyl-3-acetylindole with different substituents were investigated: (E)-3-(4-bromophenyl)-1-(1-ethyl-1H-indol-3-yl)prop-2-en-1-one (3a); (E)-3-(3-bromophenyl)-1-(1-ethyl-1H-indol-3-yl)prop-2-en-1-one (3b); (E)-1-(1-ethyl-1H-indol-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one (3c); (E)-1-(1-ethyl-1H-indol-3-yl)-3-mesitylprop-2-en-1-one (3d); and (E)-1-(1-ethyl-1H-indol-3-yl)-3-(furan-2-yl)prop-2-en-1-one (3e). The molecular packing of the studied compounds is controlled mainly by C–H⋅⋅⋅O hydrogen bonds, C–H⋅⋅⋅π interactions, and π···π stacking interactions, which were quantitatively analyzed using Hirshfeld topology analysis. Using density functional theory (DFT) calculations, the order of polarity (3b ˂ 3d ˂ 3e ˂ 3a ˂ 3c) was determined. Several chemical reactivity indices such as the ionization potential (I), electron affinity (A), chemical potential (μ), hardness (η), electrophilicity (ω) and nucleophilicity (N) indices were calculated, and these properties are discussed and compared. In addition, the antiproliferative activity of the five new chalcones was studied.

Bimetallic Iron–Palladium Catalyst System as a Lewis-Acid for the Synthesis of Novel Pharmacophores Based Indole Scaffold as Anticancer Agents

“…Michaël-type Friedel–Crafts addition of nucleophiles (especially indoles) with electron-deficient alkenes are fundamentally important chemical transformations [ 20 , 21 , 22 , 23 , 24 ]. These methods have extensive uses in the scientific work on a number of potential nucleophilic species.…”

Studies on Autophagy and Apoptosis of Fibrosarcoma HT-1080 Cells Mediated by Chalcone with Indole Moiety

“…Interestingly, the inhibition of auto agy-flux by chloroquine-sensitized cells to death upon MIPP and MOMIPP treatment visible in the decreased metabolic activity of the cells and the increased apoptosis le These are the first studies of this type to show the antitumour effects of indole-based c cones on fibrosarcoma cells. Previous research reported that specific indole-based c cones can cause cell death in glioblastoma, gastric carcinoma cells, and triple-nega breast cancer cells MDA-MB-231 [22,23].…”

Targeting Sterylglucosidase A to Treat Aspergillus fumigatus Infections

“…Pyrimidine-indole derivatives have been reported to inhibit α-glucosidase and α-amylase ( 23 ). Among the nitrogen-containing heterocycles, indole derivative compounds have been reported to have a wide range of biological activities, including antibacterial, antifungal, anticancer, and anti-HIV properties ( 24 – 27 ). However, to our knowledge, there are no inhibitors with chemical structures similar to that of hit B and its derivatives that target other β-glucosidases.…”