Abstract

NOVEL ANTIOXIDANT BIOASSAY, QSAR AND DOCKING STUDIES OF 1-PHENYL, 3-(NITRO FURAN) PROP-2-ENE-1-ONE DERIVATIVES

Ramesh Macha, Ganesh Arram, Parthasarathy Tigulla*

ABSTRACT

A novel in vitro antioxidant spectrophotometric method is visualized and implemented from the charge transfer complex. A simple, rapid and sensitive antioxidant bioassay study of chalcones was monitored at 370nm. The antioxidant property of chalcones is influenced to a great extent by two aryl structures and their substitution pattern. The hydroxyl substituent is the key group to enhance the efficacy of antioxidant activity for easy conversion of phenoxy radicals through the hydrogen transfer mechanism. Quantum chemical methods, AM1 and PM3 were used to estimate different physicochemical parameters and different QSAR models were generated. Docking studies were also performed with the active site of cyclo- oxygenase-2 to identify hydrogen bonding, hydrophobic and ionic interactions. GOLD, Auto dock and Argus lab docking results revealed that the active site residue, TYR-355 plays a key role in the formation of hydrogen bonding with chalcones. Mainly, the compound-2 has shown highest inhibitory activity against cyclo-oxygenase-2 with the formation of strong hydrogen bond interactions with the residues of active site. This chemical environment may serve as a starting point for synthesis of cyclo-oxygenase-2 inhibitors with improved efficacy.

Keywords: 1-Phenyl, 3-(Nitro Furan) prop-2-ene-1-one derivatives, free radical scavenging, anti-oxidant, QSAR, regression analysis, molecular docking