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Pseudonitroles and Their Dimeric Azodioxides
Author(s) -
Rehse Klaus,
Herpel Martin
Publication year - 1998
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/(sici)1521-4184(199802)331:2<79::aid-ardp79>3.0.co;2-9
Subject(s) - chemistry , nitric oxide , monomer , aqueous solution , nitro , chloroform , in vivo , stereochemistry , dimer , nuclear chemistry , organic chemistry , polymer , alkyl , microbiology and biotechnology , biology
Thirteen geminally substituted nitro‐nitroso compounds (pseudonitroles) have been synthesized, four of them for the first time. In the solid state the pseudonitroles are dimerized to azodioxides. This is proved by IR spectroscopy, with the dimeric N‐O valence vibration being observed between 1293 and 1306 cm –1 . Only 1,3‐diphenyl‐2‐nitro‐2‐nitrosopropane is monomeric even when solid. This is backed by its blue color and an IR band at 1574 cm –1 . When dissolved in chloroform these azodioxides dissociate completely to the blue monomers (λ max ?po 650 nm). Eight pseudonitroles inhibited the aggregation of blood platelets half‐maximally at concentrations below 10 μM (Born test, collagen). When administered orally to rats (60 mg/kg) the thrombus formation in mesenteric arterioles and venules was inhibited up to 25 percent ( k : 1‐nitro‐1‐nitrosocyclohexane). When kept in aqueous media at 37°C nitric oxide and its reduced form, i.e. nitrosohydrogen, are released. This suggests that the above biological effects arise from an NO dependent mechanism. The lack of influence on the blood pressure of spontaneously hypertensive rats, however, strongly suggests that an enzyme supported rather than a thermal formation of NO occurs in vivo .