Anticancer Indole-Based Chalcones: A Structural and Theoretical Analysis

The crystal structures of five new chalcones derived from -ethyl-3-acetylindole with different substituents were investigated: ( )-3-(4-bromophenyl)-1-(1-ethyl-1 -indol-3-yl)prop-2-en-1-one ( ); ( )-3-(3-bromophenyl)-1-(1-ethyl-1 -indol-3-yl)prop-2-en-1-one ( ); ( )-1-(1-ethyl-1 -indol-3-yl)-3-(4-me...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (20), p.3728
Main Authors: Badria, Farid A, Soliman, Saied M, Atef, Saleh, Islam, Mohammad Shahidul, Al-Majid, Abdullah Mohammed, Dege, Necmi, Ghabbour, Hazem A, Ali, M, El-Senduny, Fardous F, Barakat, Assem
Format: Article
Language:English
Subjects:
Adenocarcinoma
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor activity
Breast cancer
Carbonyl compounds
Carbonyl groups
Carbonyls
Cell Survival - drug effects
Cells, Cultured
chalcone
Chalcones - chemistry
Chalcones - pharmacology
Colorectal carcinoma
Crystal structure
cytotoxic activity
Cytotoxicity
Hydrogen Bonding
Hydrogen bonds
indole
Indoles
Indoles - chemistry
Lung carcinoma
Models, Molecular
Molecular Structure
Polymerization
Structure-Activity Relationship
Theoretical analysis
Tubulin
Tumor cell lines
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Summary:The crystal structures of five new chalcones derived from -ethyl-3-acetylindole with different substituents were investigated: ( )-3-(4-bromophenyl)-1-(1-ethyl-1 -indol-3-yl)prop-2-en-1-one ( ); ( )-3-(3-bromophenyl)-1-(1-ethyl-1 -indol-3-yl)prop-2-en-1-one ( ); ( )-1-(1-ethyl-1 -indol-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one ( ); ( )-1-(1-ethyl-1 -indol-3-yl)-3-mesitylprop-2-en-1-one ( ); and ( )-1-(1-ethyl-1 -indol-3-yl)-3-(furan-2-yl)prop-2-en-1-one ( ). 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 ( ) 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24203728