SYNTHESIS, BIOLOGICAL EVALUATION, AND DOCKING STUDY OF NOVEL 2-PHENYL-1- BENZOPYRAN-4-ONE DERIVATIVES - AS A POTENT CYCLOOXYGENASE-2 INHIBITOR

NATARAJAN KIRUTHIGA; THANGAVELU PRABHA; CHELLAPPA SELVINTHANUJA; KULANDAIVEL SRINIVASAN; THANGAVEL SIVAKUMAR

doi:10.22159/ajpcr.2019.v12i3.30466

Authors

NATARAJAN KIRUTHIGA Department of Pharmaceutical Chemistry, Nandha College of Pharmacy, Koorapalayam Pirivu, Perundurai Road, Erode - 638 052, Tamil Nadu, India.
THANGAVELU PRABHA Department of Pharmaceutical Chemistry, Nandha College of Pharmacy, Koorapalayam Pirivu, Perundurai Road, Erode - 638 052, Tamil Nadu, India.
CHELLAPPA SELVINTHANUJA Department of Pharmaceutical Chemistry, Nandha College of Pharmacy, Koorapalayam Pirivu, Perundurai Road, Erode - 638 052, Tamil Nadu, India.
KULANDAIVEL SRINIVASAN Department of Pharmaceutical Chemistry, Nandha College of Pharmacy, Koorapalayam Pirivu, Perundurai Road, Erode - 638 052, Tamil Nadu, India.
THANGAVEL SIVAKUMAR Department of Pharmaceutical Chemistry, Nandha College of Pharmacy, Koorapalayam Pirivu, Perundurai Road, Erode - 638 052, Tamil Nadu, India.

DOI:

https://doi.org/10.22159/ajpcr.2019.v12i3.30466

Keywords:

Flavone derivatives, Cyclooxygenase-2, Antioxidant, Anti-inflammatory, Molecular docking

Abstract

Objective: The inflammation and oxidative stress were related together in the generation of reactive oxygen species, which is responsible for the enhancement of inflammation associated with various chronic diseases.

Methods: The aim of this study is to synthezise and characterizes the flavones (2-phenyl-1-benzopyran-4-one) derivatives and analyzed by their docking hypothetical data as an effective anti-inflammatory mediator against cyclooxygenase-2 (COX-2) enzyme. Further, the evaluation of various in vitro antioxidant and anti-inflammatory studies was carried out.

Results: The 10 compounds were synthesized and characterized by ultraviolet, infrared, nuclear magnetic resonance, and mass spectroscopic techniques. The docking data results of these 10 flavones derivatives against COX-2 enzymes (Protein Data Bank ID: 3LN1) showed the binding energy ranging between −5.53 kcal/mol and −7.02 kcal/mol when compared with that of the standard diclofenac (−6.34 kcal/mol). The in vitro studies suggest that the lipophilic character of the side chain donor, along with the hydroxyl substituted flavones found to have significant half maximal inhibitory concentration values.

Conclusion: Based on these in silico and in vitro evaluation results, these synthesized compounds could act as a promising inhibitor to target the COX- 2 enzyme. Hence, those compounds were effective in the management of chronic diseases by exhibits free radical scavenging and anti-inflammatory property.

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