104883-60-5

Upstream product

• 26945-93-7 2-tert-butyliminomethylphenol 
• 130995-62-9 2-(2-tert-Butyl-oxaziridin-3-yl)-phenol 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 90-02-8 salicylaldehyde 
• 16649-50-6 N-tert-Butylhydroxylamine 

Relevant academic research and scientific papers

Microwave-assisted synthesis of hydroxyphenyl nitrones with protective action against oxidative stress

Oxidative stress plays an important role in neuronal death in neurodegenerative disorders such as Parkinson's disease (PD). Hydroxyphenyl nitrones, derivatives of the nitrone spin trap alpha-phenyl-N-tert-butylnitrone (PBN), were synthesized and their antioxidant, anti-inflammatory and neuroprotective activity in neural cells evaluated. These hydroxyphenyl nitrones 5-7 were synthesized by reaction of the corresponding hydroxybenzaldehyde with N-tert-butyl hydroxylamine under microwave irradiation. They showed good peroxyl free radical scavenger capacities, analyzed by oxygen radical absorbance capacity (ORAC). Also inhibited peroxynitrite-mediated tyrosine nitration of alpha-synuclein in vitro and protected human neuroblastoma (SH-SY5Y) cells against SIN-1 and 6-OHDA toxicity when micromolar concentrations were used. Besides, the hydroxyphenyl nitrones evaluated showed anti-inflammatory activity modulating nitrite production in primary neural cell cultures of astrocytes and microglia treated with lipopolysaccharide (LPS), a potent inflammatory agent. These experimental data suggest a potential therapeutic use of these hydroxyphenyl nitrones against oxygen and nitrogen reactive species involved in neurodegenerative pathology.

COMPOSITIONS COMPRISING A NITRONE COMPOUND FOR USE IN TREATING UVEITIS

Ophthalmic pharmaceutical compositions containing a pharmaceutically acceptable ophthalmic carrier and an inflammation-treating amount of a nitrone compound are disclosed. Also disclosed are methods for treating ocular inflammation conditions, such as uveitis, using pharmaceutical compositions.

Nitrogen inversion and N-O bond rotation processes in di- and tri-substituted hydroxylamines. A dynamic NMR study

The barriers to inversion in several acyclic di- and tri-substituted hydroxylamines are determined by 1H NMR band shape analysis.The barriers range from 49.1 to 66.8 kJ mol1- and are discussed in terms of a conformational process which involves nitrogen inversion and rotation around the N-O bond.The N-benzyl group with an ortho hydroxy substituent increases the nitrogen inversion barrier by 10 kJ mol-1, which indicates the requirement of breaking of the intramolecular hydrogen bond prior to inversion.

Rearrangement Reactions of Oxaziridines to Nitrones. X-Ray Crystal and Molecular Structure of N-t-Butyl-α(o-hydroxyphenyl)nitrone

Substituted N-benzylidene-t-butylamines are oxidized with m-chloroperoxybenzoic acid to oxaziridines which can rearrange to the corresponding nitrones when electron-donating groups are present in the phenyl ring.The oxaziridine-to-nitrone rearrangement, which has been considered as a 'pseudo-abnormal' reaction, can also be catalysed by Lewis acids.It has been found that the rearrangement of 2-t-butyl-3-(o-hydroxyphenyl)oxaziridine to the corresponding nitrone is of first order.The rearrangement has been investigated for different substituents in the phenyl ring, andin the case of 2-t-butyl-3-phenyloxaziridine substituted in the ortho position with electron-donating groups it has been found that the presence of protons of a Lewis acid is necessary.An X-ray structure of α-(o-hydroxyphenyl)-N-t-butylnitrone shows strong hydrogen bonding between the nitrone oxygen and the hydrogen in the hydroxy group.The oxaziridine-to-nitrone rearrangement is also analysed from a theoretical point of view using ab initio calculations.A Mulliken-population analysis of the C-O and N-O bonds in the oxaziridine ring for para-substitued 2-t-butyl-3-phenyloxaziridines shows a reduction of the C-O bond population when an electron-donating group is present in the para position of the phenyl ring compared with an electron-withdrawing group; the N-O bond populations show the reverse picture.A state-correlation diagram for the oxaziridine-to-nitrone rearrangement is also presented and the experimental and theoretical results support each other.