Structural and biological characterization of a biomolecule: (3E)-3-(2, 4, 5-trimethoxyphenyl) methylidene) - 2, 3-dihydro-4H-1-benzopyran-4-one

Abstract

The title compound, C₁₉H₁₈O₅, has been synthesized using the Claisen-Schmidt condensation reaction from the mixture of 2,3 dihydro-4H-1-benzopyran-4-one and 2,4,5 trimethoxy benzaldehyde using ethanol as solvent. The crystal has been characterized for its 3 D structure and structural parameters were elucidated via the X-ray diffraction (XRD) method. The crystallographic parameters such as bond lengths, bond angles, and torsion angles were estimated and are comparable with the literature values. Hirshfeld surfaces namely d_norm, electrostatic potential, shape index, and curvedness were analyzed to visualize and to evaluate the weak intermolecular interactions, positive and negative potential regions, C-H…π, and π…π stacking interactions, respectively. The 2 D fingerprint plots for the whole and delineated interactions were also generated to estimate their contributions to the total Hirshfeld surface. The pairwise intermolecular interactions were calculated as the sum of four scaled energy components namely electrostatic (E_ele), polarization (E_pol), dispersion (E_dis), and exchange-repulsion (E_rep), and graphically represented as energy frameworks. The energy frameworks analysis reveals that the total stabilizing energy is highly influenced by dispersion (E_dis) energy than the other components. The material has been screened for its cytotoxic effect on normal cell lines (VERO) and anticancer activity on breast cancer cell lines (MCF-7) and the material is found to be a potential candidate against cancer proliferation.

Graphical Abstract

Keywords:

• Crystal growth
• chalcone
• hirshfeld surfaces analysis
• energy frameworks
• docking
• cancer activity

Acknowledgment

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

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.