Synthesis, theoretical studies and molecular docking of a novel chlorinated tetracyclic: (Z/E)-3-(1,8-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)acrylaldehyde

Abstract ( Z/E )-3-(1,8-Dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)acrylaldehyde 2 has been investigated experimentally and theoretically. The Wittig reaction of 1,8-dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carbaldehyde 1 and (triphenylphosphoranylidene) acetaldehyde in toluene under reflux conditions resulted in compound 2 . Spectroscopic characterization of compound 2 was performed by the Fourier-transform infrared spectroscopy, nuclear magnetic resonance, and high-resolution mass spectroscopy techniques. Density functional theory (DFT) calculations were conducted to study various global and local reactive properties. The spectra were also obtained by DFT calculations and corresponding comparisons were performed to validate the level of theory. Using DFT calculations, reactivity has been studied based on frontier molecular orbitals, charge distribution, average local ionization energies, Fukui functions, and bond dissociation energies for hydrogen abstraction. Molecular dynamics simulations have been used to investigate the influence of water as a solvent for compound 2 . Finally, compound 2 was docked into the central and allosteric binding sites of the serotonin transporter enzyme and was found to be a good candidate as an antidepressant-like compound.