Synthesis of New 2,5-Di-substituted 1,3,4-Oxadiazoles Bearing 2,6-Di-tert-butylphenol Moieties and Evaluation of Their Antioxidant Activity
Abstract
:1. Introduction
2. Results and Discussion
Chemistry
No. | Compounds | Yield % | MF | HREIMS found | HREIMS calc. |
---|---|---|---|---|---|
5a | 76.1 | C23H28N2O2 | 364.2147 | 364.2151 | |
5b | 76 | C23H28N2O3 | 380.2095 | 380.2100 | |
5c | 84.2 | C24H30N2O3 | 394.2249 | 394.2256 | |
5d | 73.6 | C22H25BrN2O2 | 428.1093 | 428.1099 | |
5e | 83.1 | C22H25ClN2O2 | 384.1597 | 384.1605 | |
5f | 70 | C22H26N2O3 | 366.1938 | 366.1943 | |
5g | 80.3 | C22H24Cl2N2O2 | 418.1219 | 418.1215 | |
5h | 74.5 | C22H24Cl2N2O2 | 418.1210 | 418.1215 | |
5i | 59.9 | C24H30N2O2 | 378.2301 | 378.2304 | |
5j | 68.4 | C23H28N2O2 | 364.2144 | 364.2151 | |
5k | 81 | C22H25ClN2O2 | 384.1600 | 384.1605 |
5 | M•+ Found | M•+ calculated | m/z of base peak 100% | M•+-HNCO |
---|---|---|---|---|
5a | 364.2 | 364.21 | 349.2 | 321.1 |
5b | 380.2 | 380.21 | 380.2 | 337.1 |
5c | 394.3 | 394.22 | 394.3 | 351.1 |
5d | 428.2 | 428.10 | 413.1 | 385.1 |
5e | 384.2 | 384.16 | 369.1 | 341.1 |
5f | 366.2 | 366.19 | 366.2 | 323.1 |
5g | 418.2 | 418.12 | 403.1 | 375.1 |
5h | 418.2 | 418.12 | 403.1 | 375.0 |
5i | 378.3 | 378.23 | 378.3 | 335.1 |
5j | 364.3 | 364.21 | 349.2 | 321.1 |
5k | 384.2 | 384.16 | 369.2 | 341.1 |
3. Antioxidant Assays
3.1. FRAP Assay
3.2. DPPH Assay
3.3. Antioxidant Activity
Compound | FRAP a | DPPH Inhibition % ±SD | IC50 ± SEM b (100 µg/mL) |
---|---|---|---|
5a | 648.3 | 76.02 ± 0.059 | 41.76 ± 0.042 |
5b | 629.4 | 62.03 ± 0.327 | 50.69 ± 0.181 |
5c | 613.3 | 56.04 ± 0.187 | 54.60 ± 0.469 |
5d | 302.2 | 30.85 ± 0.166 | >100 |
5e | 640.0 | 50.44 ± 0.045 | 99.2 ± 0.032 |
5f | 2207.2 | 89.05 ± 0.024 | 15.79 ± 0.017 |
5g | 322.8 | 30.35 ± 0.038 | >100 |
5h | 212.8 | 29.26 ± 0.041 | >100 |
5i | 987.2 | 79.22 ± 0.037 | 41.27 ± 0.027 |
5j | 1538.9 | 87.21 ± 0.084 | 15.9 ± 0.054 |
5k | 500.6 | 42.14 ± 0.078 | >100 |
BHT | 488.3 | 66.03 ± 0.051 | 79.84 ± 0.036 |
Gallic acid | 2421.1 | - | - |
Ascorbic acid | 848.9 | 90.65 ± 0.122 | 22.71 ± 0.086 |
Rutin | 445.0 | - | - |
Quercetin | 2090.6 | - | - |
Trolox | 779.4 | - | - |
4. Experimental
General Information
General Synthesis of 2,6-Di-tert-butyl-4-(5-aryl-1,3,4-oxadiazol-2-yl)phenols
5. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflictts of Interest
References
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Shakir, R.M.; Ariffin, A.; Abdulla, M.A. Synthesis of New 2,5-Di-substituted 1,3,4-Oxadiazoles Bearing 2,6-Di-tert-butylphenol Moieties and Evaluation of Their Antioxidant Activity. Molecules 2014, 19, 3436-3449. https://doi.org/10.3390/molecules19033436
Shakir RM, Ariffin A, Abdulla MA. Synthesis of New 2,5-Di-substituted 1,3,4-Oxadiazoles Bearing 2,6-Di-tert-butylphenol Moieties and Evaluation of Their Antioxidant Activity. Molecules. 2014; 19(3):3436-3449. https://doi.org/10.3390/molecules19033436
Chicago/Turabian StyleShakir, Raied M., Azhar Ariffin, and Mahmood Ameen Abdulla. 2014. "Synthesis of New 2,5-Di-substituted 1,3,4-Oxadiazoles Bearing 2,6-Di-tert-butylphenol Moieties and Evaluation of Their Antioxidant Activity" Molecules 19, no. 3: 3436-3449. https://doi.org/10.3390/molecules19033436