Synthesis, characterisation, docking analysis and biological evaluation of α,α′-bis(p-dimethylaminobenzylidene)-γ- methylcyclohexanone
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Chemistry Research Centre, SSMRV Degree College, 4th 'T' Block, Jayanagar, Bangalore 560 041, India; Department of Biotechnology, PES Institute of Technology, BSK III Stage, Bangalore 560 085, India; Department of Physics, Bhavan's Sheth R. A. College of Science, Khanpur, Ahmedabad 380 001, India; Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa; Department of Chemistry, Jnana Sahyadri, Kuvempu University, Shankaraghatta 577 451, India
α,α′-bis(p-Dimethylaminobenzylidene)-γ- methylcyclohexanone (BMABMC) C25H30ON2, has been synthesised and characterised by elemental analysis, 1H and 13C NMR, mass spectroscopic techniques and X-ray diffraction (XRD) studies. The single crystal XRD studies of the title compound reveals the presence of C-H⋯O intermolecular hydrogen bonding interactions linking inversion-related molecules into a dimer forming a ring of graph set R2 2(22). The antibacterial activitiy of the compound has been screened in vitro against the organisms. To evaluate the inhibition of HIV-1 integrase activity, molecular docking was performed and the study reveals a hydrophobic interaction with the catalytic core residues showing moderate inhibitory activity on HIV-1 integrase. The semi-empirical quantum chemical calculations were also performed using MOPAC2009 (PM3) for optimization of the geometry and the chemical activity of molecule. HOMO-LUMO transition implied an electron density transfer from C-N and C-C bonds at the edge of the molecule towards C-O and C-C bonds linked to central distorted cyclohexanone ring. The HOMO-LUMO energy gap of 7.778 eV reflects the chemical activity of the molecule thereby resulting charge transfer interaction.