Synthesis and molecular docking studies of new chromane (2-(4-hydroxybenzyl) 3,5,7-trihydroxychroma-4-one) and its O-substituted analogues

Abstract

A series of 3-(O-R) substituted compounds (SI-SX) of 2-(4-hydroxybenzyl) 3,5,7-trihydroxychroma-4-one were synthesized from easily accessible starting materials such as, p-hydroxybenzaldehyde and ethyl bromopyruvate. All the ten derivatives (SI-SX) were synthesized in appropriate yields, and they were characterized by IR, 1H NMR and C NMR. Molecular docking of all the derivatives were performed using Molegro virtual docker tool 6.0.2 (MVD) tool. CYCLOOXYGENASE-2 (COX2) or PROSTAGLANDIN SYNTHASE-2 was taken as the target protein and was downloaded from Research Collaboratory for Structural Bioinformatics (RCSB) Protein Data Bank (PDB) (https://www.rcsb.org/structure/1CX2) with PDBID: ICX2, 10.2210/pdb1CX2/pdb). The 3D images of ligand protein interactions were extracted using the software, MVD 6.0.2 visualizer interface. Among all the derivatives, SII, SVI has shown good moldock score values -77.59 and -75.75 with high number of interactions (09) towards the target protein, indicating its ability to act as an anti-inflammatory and analgesic activity.