Anticancer Indole-Based Chalcones: A Structural and Theoretical Analysis

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Badria F. A., Soliman S. M., Atef S., Islam M. S., Al-Majid A. M., DEGE N., ...Daha Fazla

MOLECULES, cilt.24, sa.20, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 24 Sayı: 20
  • Basım Tarihi: 2019
  • Doi Numarası: 10.3390/molecules24203728
  • Dergi Adı: MOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: chalcone, indole, crystal structure, cytotoxic activity, ALKALOIDS
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

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...pi interactions, and pi...pi 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 (mu), hardness (eta), electrophilicity (omega) 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.