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

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journal contribution
posted on 25.11.2021, 18:00 by Yasmin Haroon Shaik, Venkataramaiah Chintha, Mohan Gundluru, Santhisudha Sarva, Suresh Reddy Cirandur

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.

Funding

One of the authors SHAIK HAROON YASMIN expresses her thanks to the Department of Science and Technology, New Delhi, India for the financial support under DST-INSPIRE Fellowship program No. DST/INSPIRE Fellowship/IF170317, dated: 24/05/2017. One of the author Dr. G Mohan acknowledges DST-PURSE 2nd Phase Programme facilitated at Sri Venkateswara University, Tirupati, India supported by Department of Science and Technology, New Delhi, India [17118-UGC-III(3)/DST-PURSE 2nd Phase/2017, Dt: 23-08-2018] for funding. One of the authors Dr. S. Santhisudha expresses her sincere thanks to DST, New Delhi, India, for providing financial support through Woman Scientist Scheme-A (WOS-A) (F. no.: SR/WOS-A/CS-104/2018, Dated: 14-09-2020).

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