Synthetic Antioxidants

Durand, Grégory

doi:10.1002/9781118355886.ch15

Cited by 3 publications

(3 citation statements)

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“…The literature is full of articles and reviews that have covered the organic [44], physicochemical/computational [45], and biological aspects of these molecules [46]. In addition, collateral topics, such as "antioxidants" [47], "ROS", and "spin-trapping agents" [48], usually include nitrones in their accounts, resulting in an impressive mass of information underlying their medicinal chemical features [49].…”

Section: Introductionmentioning

confidence: 99%

α-Phenyl-N-tert-Butylnitrone and Analogous α-Aryl-N-alkylnitrones as Neuroprotective Antioxidant Agents for Stroke

Marco-Contelles

2024

Antioxidants

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The recent advances in research on the use of the antioxidant and neuroprotective agent α-phenyl-N-tert-butylnitrone (PBN) for the therapy of stroke have been reviewed. The protective effect of PBN in the transient occlusion of the middle cerebral artery (MCAO) has been demonstrated, although there have been significant differences in the neuronal salvaging effect between PBN-treated and untreated animals, each set of data having quite large inter-experimental variation. In the transient forebrain ischemia model of gerbil, PBN reduces the mortality after ischemia and the neuronal damage in the hippocampal cornu ammonis 1 (CA1) area of the hippocumpus caused by ischemia. However, PBN fails to prevent postischemic CA1 damage in the rat. As for focal cerebral ischemia, PBN significantly reduces cerebral infarction and decreases neurological deficit after ischemia using a rat model of persistent MCAO in rats. Similarly, the antioxidant and neuroprotective capacity of a number of PBN-derived nitrones prepared in the author’s laboratory have also been summarized here, showing their high potential therapeutic power to treat stroke.

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Section: Introductionmentioning

confidence: 99%

α-Phenyl-N-tert-Butylnitrone and Analogous α-Aryl-N-alkylnitrones as Neuroprotective Antioxidant Agents for Stroke

Marco-Contelles

2024

Antioxidants

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“…Not surprisingly, in the literature there are plenty of articles/reviews that have covered the organic, physicochemical/computational, and biological aspects of these molecules. In addition, collateral topics, such as “antioxidants”, “reactive oxygenated species”, “spin-trap agents”, usually include nitrones in their accounts, resulting in a real impressive mass of information underlying key medicinal chemistry features …”

Section: Introductionmentioning

confidence: 99%

Recent Advances on Nitrones Design for Stroke Treatment

Marco‐Contelles

2020

J. Med. Chem.

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The recent advances of tetramethylpyrazine nitrones and quinolylnitrones for the treatment of stroke have been reviewed and compared with other agents, showing promising therapeutic applications. As a result of a functional transformation of natural product ligustrazine, (Z)-N-tert-butyl-1-(3,5,6-trimethylpyrazin-2-yl)methanimine oxide ( 6) is a multitarget small nitrone showing potent thrombolytic activity and free radicals scavenging power, in addition to nontoxicity and blood−brain barrier permeability. Similarly, antioxidant (Z)-N-tert-butyl-1-(2-chloro-6-methoxyquinolin-3-yl)methanimine oxide ( 17) is a novel agent for cerebral ischemia therapy as it is able to scavenge different types of free radical species, showing strong neuroprotection and reduced infarct size.

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“…The nitronyl group reacts with a free radical to form a stable and identifiable aminoxyl radical that can be detected by electron paramagnetic resonance (EPR) spectroscopy. , Two families of nitrones are commonly employed: the cyclic nitrones derived from the 5,5-dimethyl-1-pyrroline N -oxide (DMPO) and the linear variants derived from the α-phenyl- N - tert -butyl nitrone (PBN). Aside from their use as spin-traps, the ability of nitrones to prevent oxidative stress-mediated damage in in vitro, in vivo, and ex vivo models has made them promising synthetic antioxidants with considerable potential as therapeutics. − …”

Section: Introductionmentioning

confidence: 99%

α-Phenyl-N-cyclohexyl Nitrones: Preparation and Use as Spin-Traps

et al. 2016

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Two bifunctional α-phenyl-N-cyclohexyl nitrones were synthesized with the expectation that the cyclohexyl ring will impart lipophilicity to the molecule, high reactivity to the nitronyl group, and stability to the spin adducts formed. The synthesis of the acid nitrone 4 and its corresponding tert-butyl ester 3 was initiated by a Michael reaction to introduce the cyclohexyl ring. A Zn/AcOH-mediated reduction of the nitro functionality followed by condensation onto benzaldehyde generated the nitronyl function. In agreement with their high lipophilicity values, nitrone 3 was insoluble in water, while nitrone 4 exhibited a poor water solubility. It was determined that the presence of the cyclohexyl ring did not affect either the reduction or oxidation potentials of the nitronyl group in comparison to the classical α-phenyl-N-tert-butylnitrone (PBN). The spin trapping ability of 3 and 4 was investigated by EPR for oxygen- and carbon-centered radicals. In most cases, the nitrones gave rise to a standard six-line EPR spectrum whose values were in agreement with the literature, accompanied by a minor second species. In DMSO, the half-lives of nitrone 3 and 4-OOH adducts were double that of PBN, suggesting that the stabilization comes from the cyclohexyl ring and/or the electronic effect of the carboxylic acid.

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Synthetic Antioxidants

Cited by 3 publications

References 212 publications

α-Phenyl-N-tert-Butylnitrone and Analogous α-Aryl-N-alkylnitrones as Neuroprotective Antioxidant Agents for Stroke

α-Phenyl-N-tert-Butylnitrone and Analogous α-Aryl-N-alkylnitrones as Neuroprotective Antioxidant Agents for Stroke

Recent Advances on Nitrones Design for Stroke Treatment

α-Phenyl-N-cyclohexyl Nitrones: Preparation and Use as Spin-Traps

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