2-Nitrosoimino-3,6-dihydro-2H-1,3,4-thiadiazines with antiplatelet and antithrombotic properties

The successful synthesis of 17 nitrosimines of 2H-1,3,4-thiadiazines is reported. They are best characterized by their electronic spectra (lambda(max) = 504-522 nm). Some of the compounds were able to inhibit the aggregation of blood platelets in the Born-test (inducer collagen). The most active com...

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Bibliographic Details
Published inPharmazie Vol. 53; no. 12; pp. 820 - 824
Main Authors Rehse, K, Brummer, U, Unsold, E
Format Journal Article
LanguageEnglish
Published ESCHBORN GOVI-VERLAG GMBH 01.12.1998
Subjects
Animals
Capillaries - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Fibrinolytic Agents - chemical synthesis
Fibrinolytic Agents - chemistry
Fibrinolytic Agents - pharmacology
In Vitro Techniques
Life Sciences & Biomedicine
Mesentery - blood supply
Nitrosamines - chemical synthesis
Nitrosamines - chemistry
Nitrosamines - pharmacology
Pharmacology & Pharmacy
Physical Sciences
Platelet Aggregation - drug effects
Platelet Aggregation Inhibitors - chemical synthesis
Platelet Aggregation Inhibitors - chemistry
Platelet Aggregation Inhibitors - pharmacology
Rabbits
Rats
Science & Technology
Structure-Activity Relationship
Thiadiazines - chemical synthesis
Thiadiazines - chemistry
Thiadiazines - pharmacology
VASODILATING ACTIVITIES
OLIGOAMINES
NO-DONORS
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Summary:The successful synthesis of 17 nitrosimines of 2H-1,3,4-thiadiazines is reported. They are best characterized by their electronic spectra (lambda(max) = 504-522 nm). Some of the compounds were able to inhibit the aggregation of blood platelets in the Born-test (inducer collagen). The most active compound was the 3-nonyl-5-phenyl-derivative 10c which showed an IC50 = 6.5 mu mol . l(-1). In mesenteric arterioles of rats after p.o. administration (60 mg/kg) a 13% inhibition of thrombus formation is observed. The reason for the rather small effects is the high chemical stability of the title compounds and the fact that decomposition occurs mainly by the evolution of molecular nitrogen. Only small yields of NO are formed.
ISSN:0031-7144