Synthesis, quantum mechanical calculations, molecular docking, Hirshfeld surface analysis and ADMET estimation studies

Abstract

Synthesis, crystallographic characterization, spectroscopic (FT-IR, UV-Vis, NMR) and density functional studies of (E)-3-(anthracene-10-yl)-1-(napthalen-1-yl)prop-2-en-1-one (3ANP) have been reported. The molecular structure obtained from single crystal X-ray diffraction method of the investigated compound was compared with theoretical values by DFT method at B3LYP with 6-311G(d,p) basis set. The 3ANP crystallizes in triclinic space group P1 with a = 8.3426(5), b = 10.4643(6), c = 11.3925(6). Hirshfeld surface analysis was performed to confirm the existence of intra- intermolecular and other interactions using Crystal Explorer. In addition to the optimized geometrical structure, molecular electrostatic potential (MEP), natural bond orbital (NBO) analysis, non-linear optical (NLO) property, HOMO, LUMO, mulliken population analysis have been investigated. The electronic properties of the compound were examined using TD-DFT calculations. The calculated vibrational frequencies have been compared with the experimental FT-IR values. Gauge invariant atomic orbital (GIAO) method was used to calculate ¹H and ¹³C NMR chemical shifts in the ground state and was compared with the experimental NMR spectra. Further, the analysis using rules for drug-likeness and ADMET prediction revealed the druggability of the compound. Molecular docking showed the binding energy of -9.4 Kcal/mol and other interactions of 3ANP molecule with protein PDB ID: 1FCQ.

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