79108-51-3Relevant articles and documents
Transnitrosation of alicyclic N-nitrosamines containing a sulfur atom
Inami, Keiko,Kondo, Sonoe,Ono, Yuta,Saso, Chiharu,Mochizuki, Masataka
, p. 7853 - 7857 (2014/01/06)
Aromatic and aliphatic nitrosamines are known to transfer a nitrosonium ion to another amine. The transnitrosation of alicyclic N-nitroso compounds generates S-nitrosothiols, which are potential nitric oxide donors in vivo. In this study, certain alicyclic N-nitroso compounds based on non-mutagenic N-nitrosoproline or N-nitrosothioproline were synthesised, and the formation of S-nitrosoglutathione (GSNO) was quantified under acidic conditions. We then investigated the effect of a sulfur atom as the substituent and as a ring component on the GSNO formation. In the presence of thiourea under acidic conditions, GSNO was formed from N-nitrosoproline and glutathione, and an N-nitroso compound containing a sulfur atom and glutathione produced GSNO without thiourea. The quantity of GSNO derived from the reaction of the N-nitrosamines containing a sulfur atom and glutathione was higher than that from the N-nitrosoproline and glutathione plus thiourea. Among the analogues that contained a sulfur atom either in the ring or as a substituent, the thiazolidines produced a slightly higher quantity of GSNO than the analogue with a thioamide group. A compound containing sulfur atoms both in the ring and as a substituent exhibited the highest activity for GSNO formation among the alicyclic N-nitrosamines tested. The results indicate that the intramolecular sulfur atom plays an important role in the transnitrosation via alicyclic N-nitroso compounds to form GSNO.
CHIROPTICAL PROPERTIES OF N-NITROSOPYRROLIDINES AND N-NIROSAMINO ACIDS
Gaffield, William,Lundin, Robert E.,Keefer, Larry K.
, p. 1861 - 1869 (2007/10/02)
CD data for a variety of N-nitrosamino acids and N-nitrosopyrrolidines are presented.The effects of nitrosamino group conformation, pyrrolidine ring geometry, different perturbing substituents, and especially intramulecular H-bonding upon the n?* CD band are discussed.Stereochemical conclusions can be made with confidence in many cases, although no sector diagram, as yet published, succesfully correlates all the available chiroptical data in this series of compounds.However, a negative CD band due to the ??* transition was observed for all N-nitrosamines having the L-proline configuration at C-2, regardless of nitroso group conformation; it is suggested that this band be used whenever possible for stereochemical correlations.
