Synthesis, Characterization, in vitro and in silico approach of vanillin acetamides

Abstract

Abstract A sequence of biologically active vanillin acetamides bearing heterocyclic moiety (VHAs) specifically vanillin isoniazid acetamide (VISO), vanillin-2-pyridine acetamide (V2PR), vanillin-4-pyridine acetamide (V4PR) and vanillin-2-pyrimidine acetamide (V2PM) are synthesized and methodically characterized by spectroscopic techniques such as Nuclear Magnetic Resonance (1H and 13C NMR), Electrospray Ionization Mass, Fourier Transform Infrared and Ultraviolet-Visible spectroscopy. Further, the VHAs are inspected for in vitro biological activities such as anti-inflammatory by protein anti-denaturation, antidiabetic by enzyme inhibition method and the in vitro results are linked with the reference drug. The chemical structure and electronic topographies of VHAs agree with the biological activity distinctions. Hence, thorough analysis has been achieved in the computational methods such as Frontier molecular orbitals, molecular electrostatic potential and Mulliken charge distribution studies using the density functional theory method. Moreover, theoretically calculated UV-visible and FT-IR spectral data are compared with observed results signifying negligible error. The results have been used for the resolve of biomolecule interaction with exact enzymes like α-amylase (1HNY.pdb), cyclooxygenases (1PGG.pdb and 4-COX.pdb) and Bovine Serum Albumin (3V03.pdb) using molecular docking studies. The correlation between in vitro studies and docking results revealed that structural and electronic properties production an important role in biological activity. The ADMET and toxicity studies are also performed using SwissADME and ProToxII webserver to check the pharmacokinetic profile of VHAs.