An efficient nano-FGT catalyzed green synthesis of α-aminophosphonates and evaluation of their antioxidant, anti-inflammatory activity and molecular docking studies

Abstract

A green and efficient one-pot has been developed for the synthesis of a series of new diethyl-(((2,3-dihydrobenzo[b][1, 4] dioxin-6yl)amino)(substituted phenyl)methyl) phosphonates (4a-k) by the Kabachinik-Fields reaction of 2,3-dihydrobenzo[b] [1, 4]dioxin-6-amine (1) with various substituted aldehydes (2a-k) and diethyl phosphite (3) using nano ferrite supported glutathione (nano FGT) as catalyst under microwave irradiation and solvent free conditions. The synthesized compounds were evaluated for their antioxidant (DPPH & FRAP) and anti-inflammatory activity studies. Compounds 4b (naphthyl) and 4k (9-anthracenyl) showed highest antioxidant activity than that of standard ascorbic acid in DPPH method. Whereas compounds 4f (3-nitrophenyl), 4h (3-phenoxyphenyl) and 4k (9-anthracenyl) exhibited low IC50 values than that of standard ascorbic acid in and in Ferric Reducing Antioxidant Power (FRAP) studies. Compounds 4a, 4b, 4h, 4i, and 4k have shown strong anti-inflammatory activity against LPS induced cell death in RAW 264.7 cell lines. Molecular docking studies were also carried out against COX-2 showed high binding energies that are in support of their high anti-inflammatory activity. Being the most bioactive compound (4k) stands as promising next future anti-oxidant and anti-inflammatory agent.