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. 2014 Mar 20;19(3):3436-49.
doi: 10.3390/molecules19033436.

Synthesis of new 2,5-di-substituted 1,3,4-oxadiazoles bearing 2,6-di-tert-butylphenol moieties and evaluation of their antioxidant activity

Raied M Shakir  1 , Azhar Ariffin  2 , Mahmood Ameen Abdulla  3
Affiliations

Synthesis of new 2,5-di-substituted 1,3,4-oxadiazoles bearing 2,6-di-tert-butylphenol moieties and evaluation of their antioxidant activity

Raied M Shakir et al. Molecules. .

Abstract

Eleven new 2,6-di-tert-butyl-4-(5-aryl-1,3,4-oxadiazol-2-yl)phenols 5a-k were synthesized by reacting aryl hydrazides with 3,5-di-tert butyl 4-hydroxybenzoic acid in the presence of phosphorus oxychloride. The resulting compounds were characterized based on their IR, ¹H-NMR, ¹³C-NMR, and HRMS data. 2,2-Diphenyl-1-picrylhydrazide (DPPH) and ferric reducing antioxidant power (FRAP) assays were used to test the antioxidant properties of the compounds. Compounds 5f and 5j exhibited significant free-radical scavenging ability in both assays.

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Conflict of interest statement

The authors report no conflicts of interest. The authors alone are responsible for the content and writing of the paper.

Figures

Figure 1
Figure 1
Di-tert-butyl-phenols with long-chain resonance as antioxidants.
Scheme 1
Scheme 1
Synthesis of 2,6-di-tert-butyl-4-(5-aryl-1,3,4-oxadiazol-2-yl)phenols.
Figure 2
Figure 2
HMBC expansion region of 5d.
Scheme 2
Scheme 2
Proposed pathways of HNCO loss.
Figure 3
Figure 3
FRAP assay for the synthesized 2,6-di-tert-butyl-4-(5-aryl-1,3,4-oxadiazol-2-yl)phenols.
Figure 4
Figure 4
DPPH inhibitions of 5f and 5j at different concentration.
See this image and copyright information in PMC

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