Synthesis, structure determination, Hirshfeld surfaces analysis and anticancer activity study of a new biomolecule: (2E)-2-{[4-(benzyloxy)phenyl]methylidene}-3,4-dihydronaphthalen-1(2H)-one

Abstract

A new chalcone derivative (2E)-2-{[4-(benzyloxy) phenyl]methylidene}-3,4-dihydronaphthalen-1(2H) was synthesized using Claisen-Schmidt condensation reaction and crystallized by slow evaporation method at ambient temperature. The structure of the title compound was determined by the single-crystal X-ray diffraction (XRD) technique. Hirshfeld surfaces mapped over the properties d_norm, electrostatic potential,shape index, curvedness, fragment patches, 2 D fingerprint plots, and the energy frameworks were generated and analyzed. The red spots on the d_norm surface indicate weak intermolecular interactions such as hydrogen bonds, π…π and C-H…π contacts. The C-H…π stacking is visualized as adjacent red and blue triangles in the shape index, and by flat regions in the curvedness property. From the 2 D fingerprint plots, the contribution to the total Hirshfeld surface due to the H…H contacts was found to be the highest with 51.7% followed by C···H/H···C (33.9%), and H···O/O···H(12.2%) contacts. The energy framework analysis reveals that the dispersion energy contribution is the most to the total energy than the other component energies. In-vitro and in-silico anti-proliferative activity of the prepared compound showed excellent anti-cancer activity on MCF-7 cell lines at a concentration of 15.6 µg/mL with 50.86% of cell viability. The molecular docking analysis showed the best binding affinity between the compound and the target protein.

GRAPHICAL ABSTRACT

Keywords:

• Crystal structure
• chalcone
• Hirshfeld surfaces analysis
• anti-cancer activity

Acknowledgements

The authors thank the Central Instrumentation Facility (DST– FIST), Queen Mary's College (A), Chennai-4 for the computing facility and SAIF, IIT, Madras, for the X-ray data collection facility.

Disclosure statement

The authors declare that they have no conflicts of interest.