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New NO‐Donors with Antithrombotic and Vasodilating Activities, IV: Chemical Reactivity of Nitrosimines and its Implications for their Pharmacologic Properties
Author(s) -
Rehse Klaus,
Schleifer KlausJürgen,
Lüdtke Eberhard,
Böhme Eyke
Publication year - 1994
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19943270603
Subject(s) - chemistry , imine , thiazole , medicinal chemistry , bond cleavage , methanol , glutathione , reactivity (psychology) , amine gas treating , stereochemistry , organic chemistry , catalysis , enzyme , medicine , alternative medicine , pathology
Abstract Nitrososydnone‐5‐imines and Thiazole‐2‐nitrosimines are susceptible to photolytic cleavage of the NNO 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 N 2 O were detected in the head space of the reaction vials when oxygen was excluded. The formation of N 2 O 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 that the nitroxylate anion NO − plays an important role in the stimulation of s‐GC.