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Articles

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

ORCID Icon, , , , ORCID Icon & ORCID Icon
Pages 269-275 | Received 29 Apr 2021, Accepted 07 Dec 2021, Published online: 17 Dec 2021
 

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 dnorm, electrostatic potential,shape index, curvedness, fragment patches, 2 D fingerprint plots, and the energy frameworks were generated and analyzed. The red spots on the dnorm 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

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.

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