Structural, spectroscopic (NMR, FTIR, UV), Quantum chemical calculations and drug docking studies of 6-amino benzoxazol-2(3H)-one

Abstract

Abstract The aromatic organic benzoxazole molecule seems to have a wide variety of biological activities. The benzoxazole derivatives are pharmaceutically active ingredients and a vital building block in the field of medicine and agricultural sciences. An amine derivative of 2-Benzoxazoline having an empirical formula C7H6N2O2 was chosen for the present study. The chemical structure and composition of the title molecule have been investigated by using numerous techniques like UV-visible, FT-Raman, FT-IR, 1H, 13C NMR. The study of single crystal X‒ray diffraction reports that the compound is crystallized in monoclinic P21 space group with cell dimensions a=4.292 A, b=12.333 A, c=6.398 A, α=90°, β=103.605°, γ=90°. The Density Functional Theory (DFT) has been used to know the electronic structure of the molecule. The structural parameters of the title compound have been obtained from the experimental findings and compared with DFT theoretical values. The DFT model predicted a possible existence of tautomers for 6-Amino benzoxazol-2(3H)-one which is further confirmed with the help of vibrational and NMR spectral studies. These results suggested that the tautomers are the key factors to determine the overall chemical significance of the title compound. Further, the drug docking studies were also employed with Auto Dock tool to conclude its efficiency, binding mode, and nature of chemical interactions of title ligand molecule by the target proteins. The binding efficiency of the Lactam form of ligand on the receptor was found to be superior to the Lactim form of 6-Amino Benzoxazol-2(3H)-one.