139607-30-0

Upstream product

• 594-70-7 2-Methyl-2-nitropropane 
• 456-48-4 3-Fluorobenzaldehyde 
• 16649-50-6 N-tert-Butylhydroxylamine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 

Relevant academic research and scientific papers

PBN (phenyl-N-tert-butylnitrone)-derivatives are effective in slowing the visual cycle and rhodopsin regeneration and in protecting the retina from light-induced damage

A2E and related toxic molecules are part of lipofuscin found in the retinal pigment epithelial (RPE) cells in eyes affected by Stargardt's disease, age-related macular degeneration (AMD), and other retinal degenerations. A novel therapeutic approach for t

Iridium-Catalyzed Direct C-H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature

Ir(III)-catalyzed direct C-H sulfamidation of aryl nitrones has been developed to synthesize various sulfamidated nitrones in moderate to excellent yields with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly at room temperature with low catalyst loading in the absence of external oxidants, acids, or bases. Molecular nitrogen was released as the sole byproduct, thus providing an environmentally benign sulfamidation process. And this protocol could efficiently apply to synthesize the substituted benzisoxazoline via one-step transformation from the product.

Stereoselective synthesis of fluoroalkenoates and fluorinated isoxazolidinones: N-substituents governing the dual reactivity of nitrones

α-Fluoroalkenoates and 4-fluoro-5-isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones by the reactions between nitrones and α-fluoro-α-bromoacetate. By altering N-substituents in nitrones, (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones can be achieved, respectively, with high chemo- and stereoselectivities. Experimental and computational studies have been conducted to elucidate the reaction mechanisms. Linear free energy relationship studies further revealed that the N-substituent effects are primarily of electronic origin. Copyright

COMPOSITIONS AND METHODS OF INHIBITING RETINAL DEGENERATION

Nitrone-based compositions are disclosed that may be utilized for the prevention and treatment of a variety of ophthalmic diseases or conditions where RPE65 protein isomerohydrolase is implicated. Methods of production and use of said nitrone-based compos

Electronic properties of the nitrone substituent. Stabilization of benzylic carbocations

The nitrone substituent CH=N(O) t-Bu is electron-withdrawing with a Taft σI value of 0.20. It also retards the solvolysis rate of a cumyl chloride when placed in the meta-position (σ = 0.20). However, CH=N(O) t-Bu becomes weakly cation stabilizing when placed in the para-position of a cumyl cation (σ+ = -0.04). This weak cation stabilization is a result of a conjugative interaction which delocalizes charge and offsets the inductive effect of the nitrone. When the nitrone is placed in the para-position, but then twisted out of conjugation with the aromatic ring by incorporation of flanking 3,5-dimethyl groups, it again retards solvolysis rates. Computational studies (B3LYP/6-31G*) show that the nitrone substituent stabilizes a para-substituted benzyl cation relative to the meta-substituted analog by a conjugative interaction. However, the calculated stabilization greatly overestimates the cation stabilization seen in solvolytic reactions. Copyright

Nitrone derivatives

A compound represented by the figure (1) or a pharmaceutically acceptable salt thereof is useful as medicament for treating retinal degenerative disorders: wherein Ar is optionally substitued phenyl or optionally substituted heteroaryl;. n is 0, 1 or 2; W

Synthesis and Characterization of Phenyl-Substituted C-Phenyl-N-tert-butylnitrones and Some of Their Radical Adducts

Synthesis of C-phenyl-N-tert-butylnitrone (PBN) and several of its analogues with substituents in the 2-, 3-, or 4-position on the phenyl ring is described.While a one-pot reduction/condensation method proved suitable for the most compounds, it was necessary to prepare some examples by direct condensation or through oxidation of the appropriate imine.The 1H NMR data for the 3-X- and 4-X-PBN's can be correlated with the Hammett equation.For the 3-X series Δδ for the α-proton correlates best with ?+ and has a correlation coefficient of 0.90.For the 4-X series a dual substituent parameter equation using ?R0 gives the best correlation with r = 0.99.The hyperfine splitting constants (hfsc's) of HO and HOO adducts of serveral substituted PBN's are also included and their correlation with the Hammett equation is discussed.