83326-65-2Relevant academic research and scientific papers
Synthesis of N-substituted N-nitrosohydroxylamines as inhibitors of mushroom tyrosinase
Shiino, Mitsuhiro,Watanabe, Yumi,Umezawa, Kazuo
, p. 1233 - 1240 (2007/10/03)
A series of N-substituted N-nitrosohydroxylamines including six new compounds were synthesized and examined for inhibition of mushroom tyrosinase. Corresponding hydroxylamines were reacted with n-butyl nitrite to give substituted nitrosohydroxylamines as their ammonium salt. The N-substituted hydroxylamines were prepared from the primary amines via the oxaziridine, or from the carbonyl compounds via the oxime. Most of the nitrosohydroxylamines tested inhibited mushroom tyrosinase. Among them, N-cyclopentyl-N-nitrosohydroxylamine exhibited the most potent activity (IC50=0.6 μM), as powerful as that of tropolone, one of the most powerful inhibitors. As removal of nitroso or hydroxyl moiety, the enzyme inhibitory activity was completely diminished. Both N-nitroso group and N-hydroxy group were suggested to be essential for the activity, probably by interacting with the copper ion at the active site of the enzyme. Lineweaver-Burk plotting showed that cupferron was a competitive inhibitor but that N-cyclopentyl-N-nitrosohydroxylamine was not.
Stereochemical and Mechanistic Aspects of the Base-catalysed Decomposition of N-Alkyloxaziridines to form NH Ketimines
Boyd, Derek R.,McCombe, Kenneth M.,Sharma, Narain D.
, p. 867 - 872 (2007/10/02)
The synthesis of a new range of oxaziridines (18)-(23), (30)-(35) by peracid oxidation of diaryl ketimines and aryl aldimines is reported.Relatively stable NH ketimine products (24)-(27) have been isolated from base-catalysed decomposition of the oxaziridines (18)-(20), (30)-(35) and a primary kinetic isotope effect (ca. kH/kD 6.0) was observed during decomposition of the oxaziridine trans-(31).The trans-oxaziridines (31)-(35) were found to decompose at a faster rate than the corresponding cis isomers.The relative rates of base-catalysed decomposition of oxaziridine stereoisomers are consistent with a mechanism involving an α-C-H proton abstraction mechanism.
