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.

In vitro and in vivo Antidiabetic Evaluation of Synthesised Novel New Chromane and its Derivatives

“…13 Therefore, this novel compound was synthesized at laboratory in order to improve its % yield and further explore its biological activity. 15 This study was performed for in vitro and in vivo antidiabetic investigation of synthesized new chromane and its analogues (S23-S32) by following α-amylase, α-glucosidase and streptozotocin induced method respectively. Streptozotocin induces hyperglycaemia by impairing the glucose oxidation via inhibiting synthesis of insulin as of the pancreatic β-cells damage through alkylation of DNA chain and unnecessary generation of free radicals.…”

“…Literature reported synthesised new chromane and its analogues, S23-32 (Table 1) were investigated for in vitro hypoglycaemic effect and in vivo antidiabetic activity respectively. 15…”

“…13 To explore the diversity of chromanone nuclei, new chromane and its O-substituted analogues were synthesised at laboratory scale with good yield and purity. 15 Furthermore, using reported literature data; synthesized new chromane and its analogues (S23-S32) were investigated for in vitro and in vivo antidiabetic effect in terms of measuring hypoglycaemic level respectively. 15…”

“…15 Furthermore, using reported literature data; synthesized new chromane and its analogues (S23-S32) were investigated for in vitro and in vivo antidiabetic effect in terms of measuring hypoglycaemic level respectively. 15…”