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Current Chemical Biology

Author(s): Thanuja Balasundaram*, Kavasseri Ganesan Kripa, Thiyagarajan Bhavadharani and Charles Kanagam

DOI: 10.2174/2212796816666220517103230

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The Effect of Substituents and Functional Groups on Enhancing the Antioxidant Activity of Benzoin Derivatives

Page: [70 - 80] Pages: 11

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Abstract

Background: 2-phenyl hydrazine-1-hydroxy, 1-[2-chlorophenyl] -2-4’-methoxyphenyl] ethane and 2-oxime-1-hydroxy, 1-[2-chlorophenyl] -2-4’-methoxyphenyl] ethane derivatives of benzoin have been synthesized from 2’chloro-4-methoxy benzoin by addition reaction. Structural elucidation of the synthesized compounds was carried out through FT-IR, FT-NMR studies. The presence of electron-withdrawing and electron-donating groups enhanced the antioxidant activity, which was analyzed by 2,2-diphenyl-1-picrylhydrazyl assay, 2,2'-azino-bis (3-ethylbenzothiazoline-6- sulfonic acid) scavenging assay, hydrogen peroxide radical scavenging assay, and Ferric reducing antioxidant power assay methods. The effect of functional groups and substituents in the core structure was studied and compared with its parent compound.

Aim and Objective: In this manuscript, two derivatives of benzoin viz. 2-phenyl hydrazine-1-hydroxy, 1-[2-chlorophenyl] -2-[4’-methoxyphenyl] ethane and 2-oxime-1-hydroxy, 1-[2-chlorophenyl]-2-[4’- methoxyphenyl] ethane (HA) derivatives were synthesized by benzoin condensation and followed by addition reaction to find a potential anti-oxidant agent.

Materials and Methods: Qualitative analyses were determined by FT-IR and FT-NMR studies. Antioxidant activities were tested by DPPH assay, ABTS assay, and FRAP assay H2O2 methods.

Results: From the obtained results, it is confirmed that the effect of withdrawing and electron releasing groups as a substituent in the core structure of parent compounds enhances the activity of antioxidant. The role of substituents is discussed in detail.

Conclusion: The results of the biochemical assay reveal that the synthesized compounds serve as good free radical inhibitors and scavengers, which inhibit the oxidative reactions, and are responsible for cell damage, food spoilage, etc. The promising anti-oxidant activities are because of the effective substituents which play a prominent role in the drug industries.

Keywords: FT-IR, FT-NMR, DPPH, ABTS, FRAP assay, benzoin derivatives.

Graphical Abstract

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