Synthesis, characterization, Hirshfeld surface analysis and molecular docking studies of 3-(cyclohexylthio)-4-hydroxy-6-methyl-2H-chromen-2-one

Abstract

The 3-(cyclohexylthio)-4-hydroxy-6-methyl-2H-chromen-2-one (mf. C16H18O3S), a biologically relevant new version of organo-sulfur compounds, has been synthesized Its detailed spectral properties and X-ray crystal structure are studied. The crystal structure was solved by direct method and refined by full matrix least squares procedure to final R value of 0.0468. The crystal structure is stabilized by elaborate system of O-H···O, C-H···O, O-H···S hydrogen bonds to form supramolecular structures. 3D Hirshfeld surfaces and allied 2D fingerprint plots were analyzed for molecular interactions. The Hirshfeld surface analysis of the crystal structure indicates H…H and C···H/H···C interactions as the most important contributors to the crystal packing. Theoretical (DFT) studies on the molecular structure, HOMO, LUMO, MESP surfaces have been performed at B3LYP/6-311 + G(d,p) level of theory. The molecular docking studies have been performed to get insights into the inhibition nature of this molecule against CDKS protein, and search for new anticancer agents. Pharmacological analysis was carried out inorder to check the bioactive nature of the synthesized compound.