3684-97-7Relevant academic research and scientific papers
New NO-donors with antithrombotic and vasodilating activities, IV: Chemical reactivity of nitrosimines and its implications for their pharmacologic properties
Rehse,Schleifer,Ludtke,Bohme
, p. 359 - 364 (1994)
Nitrososydnone-5-imines and Thiazole-2-nitrosimines are susceptible to photolytic cleavage of the =N-NO bond. This can be achieved with a tungsten lamp. In water the corresponding syndnone imine salts are formed in 90% yield at 37°C. Only at higher temp. (70°C) ring opening is observed. In methanol about 25% of sydnones are obtained. On the other hand NO. and N2O were detected in the head space of the reaction vials when oxygen was excluded. The formation of N2O from nitrososydnone imine was increased up to elevenfold by glutathione while the amount of NO. was decreased. In the presence of light and thiols soluble guanylate cyclase (s-GC) was stimulated. The results suggest tnat the nitroxylate anion NO- plays an important role in the stimulation of s-GC.
A Model for Metabolic Activation of Dialkylnitrosoamines. Oxidative Dealkylation 2-(N-Nitrosoalkylamino)acetonitriles by a Flavin Mimic in Aqueous Solution
Yano, Yumihiko,Yokoyama, Takeshi,Ikuta, Masato,Yoshida, Kitaro
, p. 5606 - 5610 (2007/10/02)
It is found for the first time that a flavin mimic, benzodipteridine (BDP), reacts with 2-(N-nitrosoalkylamino)acetonitriles via oxidative dealkylation to yield the corresponding alcohols (ROH) and the 2-e-reduced BDP in aqueous acetonitrile.Kinetic studies reveal that the rates are first order with respect to and ->, respectively.Kinetic isotope effects (kH/kD) for RN(NO)CD2CN (R = Me, n-Bu, Ph, and PhCH2) are found to be 2.2-4.2, indicating that deprotonation is involved in the rate-determining step.The mechanism of the oxidative dealkylation of the nitrosoamines by the flavin mimic is discussed.
A SYDNONEIMINE BASE
Ogorodnikova, V. V.,Kholodov, L. E.,Yashunskii, V. G.
, p. 598 - 602 (2007/10/02)
It was shown by means of the UV spectra that a sydnoneimine base is formed from 3-cyclohexyl sydnoneimine hydrochloride by the action of an equivalent amount of sodium hydroxide in solutions of absolute alcohols.The sydnoneimine base is also formed in the case of solvolysis of N6-trimethylsilyl-3-cyclohexylsydnoneimine in methanol.The sydnoneimine base in solutions exists in equilibrium with the chain isomer, viz., the nitrile.The fraction of the cyclic isomer increases as the electron-donor properties of the substituent in the 3 position become more pronounced.
