α-Aryl-N-aryl nitrones: Synthesis and screening of a new scaffold for cellular protection against an oxidative toxic stimulus

Melatonin and Nitrones As Potential Therapeutic Agents for Stroke

“…In fact and in addition, tert -butylnitrones, such as NXY-059, are known to afford t -butylhydroxylamines as powerful radical scavengers, after hydrolysis, that further could be oxidized to 2-methyl-2-nitrosopropane which then may synthesize NO radical, the source and origin of the neuroprotection, as it has been already reported for NO donors (Godínez-Rubí et al, 2013). Recently reported new developments have highlighted the not previously described and powerful neuroprotective effect shown by new PBN derivatives bearing N -aryl substituents on human neuroblastoma cells, under induced in vitro experimental oxidative stress (Matias et al, 2016). …”

NO and HNO donors, nitrones, and nitroxides: Past, present, and future

“…Neuroprotection was evaluated on SH‐SY5Y cells under oxidative stress, and nitrone derivatives 29a–b significantly prevented cell death induced by H 2 O 2 300 μM (28.5% of necrotic cells in control experiments vs. 11.2–5.2% in treated cells). Moreover, derivatives 29a–b led to an increase of reduced GSH levels by 65% …”

“…New α‐aryl‐ N ‐aryl nitrone derivatives (compounds 29a–b , Table ) were also recently developed . In these systems, the introduction of N ‐nitrone aryl substituents focused on two previously unexplored aspects: conformation restriction and the electron stabilization by double bond conjugation system.…”

Synthetic Studies Toward a Novel Hydroxylamine of Potential Utility in the Preparation of Mitochondriotropic Nitrones

“…Proposed synthetic strategy for compound (17) Another alternative approach to proceed with this investigation, will be the direct coupling of nitro amide (7) with the aldehyde moiety of nitrone (15) through the use of elemental zinc in ethanolic solution 76 . Although this synthetic methodology was performed on nitroarenes, it is a reasonable approach since the conversion of nitroalkanes to hydroxylamine can also be accomplished via the use of elemental zinc (Scheme 14)…”

“…Besides trying other reduction methodologies, it is also suggested to study this precursor for the direct one-pot reductive synthesis of new mitocondriotropic nitrones. Recent literature containes a report of a unique synthetic methodology describing the synthesis of alpha-aryl-N-nitrones by direct coupling of aryl aldehydes with nitro arenes through the use of elemental zinc in ethanolic solution 76 . With this in mind, it is highly recommended to examine this approach though direct coupling of (7) with the aldehyde moiety of a parent pseudoazulenyl nitrone (15) in order to create a new class of pseudoazulenyl mitochondriotropic nitrones.…”