170810-86-3

Upstream product

• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 55738-75-5 (2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol 
• 19971-12-1 3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine Hydrobromide 
• 70473-81-3 2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid methyl ester 
• 213474-58-9 1-oxyl-3-[N-(1-adamantyl)aminomethyl]-2,2,5,5-tetramethyl-3-pyrroline 
• 123665-64-5 (2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)-methanol 
• 171295-31-1 3-(N-Methoxy-N-methylcarbamoyl)-2,2,5,5-tetramethylpyrroline 
• 71051-83-7 3-formyl-2,2,5,5-tetramethyl-pyrroline-1-oxyl 

Relevant academic research and scientific papers

Synthesis of nitroxide containing polyenes: two chemically modified retinals and their interaction with bacterioopsin

The synthesis and spectroscopic characterization of two retinal analogues is described, the paramagnetic 3-pyrrolin-1-yloxy analogue 1 and its diamagnetic equivalent, the 3-pyrroline analogue 2.Various aspects of the synthesis of the aminoxy group containing polyenes are discussed.Upon interaction with bacterioopsin, both 1 and 2 are incorporated in the protein and form a system with λmax 459 nm.Neither of the two bacteriorhodopsin analogues is photoactive.ESR spectroscopy data of the system containing 1 show that the ring part of the chromophore in the protein is rigidly fixed in orientation.

Selective reduction of nitrones and nitroxides to functionalized secondary amines

Nitrones and nitroxides were selectively reduced with Fe/AcOH to secondary amines in the presence of different functional groups (aldehyde, nitrile, carboxylic ester, activated and nonactivated double or triple bonds).

Studies of structure-activity relationship of nitroxide free radicals and their precursors as modifiers against oxidative damage

The protective effects of stable nitroxides, as well as their hydroxylamine and amine precursors, have been tested in Chinese hamster V79 cells subjected to H2O2 exposure at fixed concentration or exposure to ionizing radiation. Cytotoxicity was evaluated by monitoring the viability of the cells assessed by the clonogenic assay. The compounds tested at fixed concentration varied in terms of ring size, oxidation state, and ring substituents. Electrochemical studies were carried out to measure the redox midpoint potentials. The studies show-that in the case of protection against H2O2 exposure, the protection was determined-by the ring size, oxidation state, and redox midpoint potentials. In general the protection factors followed the order nitroxides > hydroxylamines > amines. Both the six- membered ring nitroxides and substituted five-membered ring nitroxides were efficient protectors. For six-membered ring nitroxides, the compounds exhibiting the lowest midpoint potentials exhibited maximal protection. In the case of X-radiation, nitroxides were the most protective though some hydroxylamines were also efficient. The amines were in some cases found to sensitize the toxicity of aerobic radiation exposure. The protection observed by the nitroxides was not dependent on the ring size. However, the ring substituents had significant influence on the protection. Compounds containing a basic side chain were found to provide enhanced protection. The results in this study suggest that these compounds are novel antioxidants which can provide cytoprotection in mammalian cells against diverse types of oxidative insult and identify structural determinants optimal for protection against individual types of damage.