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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???? interactions, and ?···? 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 (?), hardness (?), electrophilicity (?) 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.

SUBMITTER: Badria FA 

PROVIDER: S-EPMC6832658 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Anticancer Indole-Based Chalcones: A Structural and Theoretical Analysis.

Badria Farid A FA   Soliman Saied M SM   Atef Saleh S   Islam Mohammad Shahidul MS   Al-Majid Abdullah Mohammed AM   Dege Necmi N   Ghabbour Hazem A HA   Ali M M   El-Senduny Fardous F FF   Barakat Assem A  

Molecules (Basel, Switzerland) 20191016 20

The crystal structures of five new chalcones derived from <i>N</i>-ethyl-3-acetylindole with different substituents were investigated: (<i>E</i>)-3-(4-bromophenyl)-1-(1-ethyl-1<i>H</i>-indol-3-yl)prop-2-en-1-one (<b>3a</b>); (<i>E</i>)-3-(3-bromophenyl)-1-(1-ethyl-1<i>H</i>-indol-3-yl)prop-2-en-1-one (<b>3b</b>); (<i>E</i>)-1-(1-ethyl-1<i>H</i>-indol-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one (<b>3c</b>); (<i>E</i>)-1-(1-ethyl-1<i>H</i>-indol-3-yl)-3-mesitylprop-2-en-1-one (<b>3d</b>); and (<i>E</  ...[more]

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