Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemistry
2.1.1. General Information
2.1.2. Synthesis of 2-Azidoacetaldehyde Diethyl Acetal 11
2.1.3. General Procedure for the Synthesis of (1,2,3-Triazole)Acetaldehyde Diethyl Acetals 10a–f
1-(2,2-Diethoxyethyl)-4-Phenyl-1H-1,2,3-Triazole (10a)
1-(2,2-Diethoxyethyl)-4-(2-Fluorophenyl)-1H-1,2,3-Triazole (10b)
1-(2,2-Diethoxyethyl)-4-(3-Fluorophenyl)-1H-1,2,3-Triazole (10c)
1-(2,2-Diethoxyethyl)-4-(4-Fluorophenyl)-1H-1,2,3-Triazole (10d)
1-(2,2-Diethoxyethyl)-4-(2,4-Difluorophenyl)-1H-1,2,3-Triazole (10e)
1-(2,2-Diethoxyethyl)-4-(4-Fluoro-3-Methylphenyl)-1H-1,2,3-Triazole (10f)
2.1.4. General Procedure for the Synthesis of Nitrones 8a–f and 9a–f
N-(2-(4-Phenyl-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8a)
N-(2-(4-(2-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8b)
N-(2-(4-(3-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8c)
N-(2-(4-(4-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8d)
N-(2-(4-(2,4-Difluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8e)
N-(2-(4-(4-Fluoro-3-Methylphenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8f)
2-Methyl-N-(2-(4-Phenyl-1H-1,2,3-Triazol-1-yl)Ethylidene)Propan-2-Amine Oxide (9a)
N-(2-(4-(2-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9b)
N-(2-(4-(3-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9c)
N-(2-(4-(4-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9d)
N-(2-(4-(2,4-Difluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9e)
N-(2-(4-(4-Fluoro-3-Methylphenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9f)
2.2. Estimation of Lipophilicity as Clog P
2.3. Antioxidant Assays
2.3.1. Materials and Methods
2.3.2. Inhibition of Linoleic Acid Peroxidation
2.3.3. In Vitro Inhibition of Soybean Lipoxygenase (LOX)
2.3.4. Competition of Nitrones 8 and 9 with DMSO for Hydroxyl Radicals
2.3.5. ABTS∙+–Decolorization Assay in Ethanolic Solution for Antioxidant Activity
3. Results and Discussion
3.1. Chemistry
3.2. Antioxidant Activity of Nitrones 8a–f and 9a–f
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
References
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Nitrones/ Standards | Clog P b | LOX Inhibition (% a or IC50 [µM]) | ILP (%) a | Scavenging Activity for HO• (%) a | ABTS+∙ (%) a |
---|---|---|---|---|---|
8a | 0.21 | 37.5 μM | 48.4 | 93 | 14 |
8b | 0.39 | 24% | 2 | 61 | 13 |
8c | 0.39 | 40% | 65 | 59 | no |
8d | 0.39 | no | 54 | 80 | 5.3 |
8e | 0.54 | 87.5 μM | 87 | 76 | no |
8f | 0.59 | 44 % | 41 | 91.5 | 34.3 |
9a | 1.44 | 44% | 74.5 | 76 | 4 |
9b | 1.62 | 40 μM | 73 | 76 | no |
9c | 1.44 | no | 21 | 89 | no |
9d | 1.62 | 100 μM | 29 | 99 | no |
9e | 1.42 | 100 μM | 100 | 100 | no |
9f | 2.12 | 27 μM | 87 | 99.9 | 16 |
NDGA | 87 (0.45 μM) | ||||
Trolox | 93 | 88 | 91 | ||
PBN | 23% | 11 | no | 5 |
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Hadjipavlou-Litina, D.; Głowacka, I.E.; Marco-Contelles, J.; Piotrowska, D.G. Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones. Antioxidants 2023, 12, 36. https://doi.org/10.3390/antiox12010036
Hadjipavlou-Litina D, Głowacka IE, Marco-Contelles J, Piotrowska DG. Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones. Antioxidants. 2023; 12(1):36. https://doi.org/10.3390/antiox12010036
Chicago/Turabian StyleHadjipavlou-Litina, Dimitra, Iwona E. Głowacka, José Marco-Contelles, and Dorota G. Piotrowska. 2023. "Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones" Antioxidants 12, no. 1: 36. https://doi.org/10.3390/antiox12010036
APA StyleHadjipavlou-Litina, D., Głowacka, I. E., Marco-Contelles, J., & Piotrowska, D. G. (2023). Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones. Antioxidants, 12(1), 36. https://doi.org/10.3390/antiox12010036