Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of <i>β</i>-Enaminonitrile Incorporating 1<i>H</i>-Benzo[<i>f</i>]Chromene Moiety

Abstract

In this work, we used microwave irradiation conditions to synthesize β-enaminonitrile (4), which was affirmed using single crystal X-ray diffraction and the different spectral data. Two tumor cell lines, MCF-7 and MCF-7/ADR, as well as two normal cell lines, HFL-1 and WI-38, were used to assess the anticancer activity of compound 4. The studied molecule exhibited potent efficacy against the MCF-7 and MCF-7/ADR cell lines compared with the reference drugs. Furthermore, target compound 4 had feeble activity against HFL-1 and WI-38. The chemical reactivity was discussed using DFT and QTAIM analysis to study the intrinsic electronic properties of compound 4. A molecular docking study was also conducted to examine their binding affinity to the EGFR. Compound 4 revealed a stable binding mode at the enzyme active pocket more than the reference inhibitor. The docking analysis was performed for molecule (4).

Keywords

• β-enaminonitrile
• microwave irradiation
• X-ray
• antitumor activity
• docking study