Structural, Hirshfeld, spectroscopic, quantum chemical and molecular docking studies on 6b′, 7′, 8′, 9′-Tetrahydro-2H,6′H-spiro[acenaphthylene-1,11′-chromeno [3,4-a]pyrrolizine]-2,6′(6a′H,11a′H)-dione

Abstract

In the present study, a novel 6b′, 7′, 8′, 9′-Tetrahydro-2H,6′H-Spiro [acenaphthylene-1,11′-chromeno [3,4-a] pyrrolizine]-2,6′ (6a′H,11a′H)- dione (ACPD) single crystal was grown by the slow evaporation method. The single crystal X-ray diffraction analysis and density functional theory (DFT) calculations were carried out for the ACPD molecule. The ACPD crystallizes in the orthorhombic space group Pbca with a = 18.3519 (14) Å, b = 11.3883 (9) Å, c = 18.3545 (14) Å. Hirshfeld surface analysis and finger print plots were analysed using Crystal Explorer to confirm the existence of intermolecular, intramolecular and other weak interactions. The molecular geometry (X-ray coordinates) was optimized using Density Functional Theory (DFT/B3LYP) method with the 6-31G+ (d, p) basis set using Gaussian 09 W software. The optimized geometrical parameters, structures and vibrational wavenumbers were compared with the experimental results. Natural Bond Orbital analysis (NBO) was carried out to evaluate the intramolecular stabilization interactions of the molecule. The highest occupied molecular orbital (HOMO) energy, the lowest unoccupied molecular orbital (LUMO) energy and their energy gap (ΔE) of the ACPD molecule were calculated. In addition, the molecular docking analysis was carried out to explore the inhibitory nature of the molecule against Cdc7 kinase, CK2 and PPARγ. Docking results suggest that su the ACPD molecule could be a novel inhibitor candidate of PPARγ receptor which causes type 2 diabetes mellitus.