New NO-Donors with Antithrombotic and Vasodilating Activities, V: Oligonitroso Sydnone Imines

Autor:	Klaus Rehse, Klaus-Jürgen Schleifer, Antje Martens, Michael Kämpfe
Rok vydání:	1994
Předmět:	Stereochemistry Vasodilator Agents Substituent Pharmaceutical Science Nitroso Sydnones Rats chemistry.chemical_compound Fibrinolytic Agents chemistry Drug Discovery Animals Sydnone imine Moiety Platelet aggregation inhibitor Methylene Sydnone Platelet Aggregation Inhibitors Fibrinolytic agent
Zdroj:	Archiv der Pharmazie. 327:393-397
ISSN:	1521-4184 0365-6233
DOI:	10.1002/ardp.19943270610
Popis:	Nine 4,4'-bis- and four 4,4'-tris-N-nitroso syndrome imines were synthesized. The sydnone imine moiety is connected either by aromatic 1,3-phenylene or 1,3,5-benzene or aliphatic methylene or propylene bridges. Compared to the corresponding sydnone imines the collagen induced platelet aggregation inhibiting activity is increased by several orders of magnitude by the nitroso derivatives. The most potent compound bears a hexyl substituent in 3-position (1d: IC50 = 0.05 mumol/L). These data show that aromatic bridges (1d, 2d) are more favourable than aliphatic ones (4b). This indicates the mutual influence of the nitroso-imino moieties via the aromatic bridges. In the series of 3,3'-bis-nitrososydnone imines (13 compounds) mostly additive effects of the nitroso groups are seen. The activities range from IC50 = 0.2 mumol/L (5i; 1,3-xylene bridge) to IC50 = 8 mumol/L (5b; trimethylene bridge). The differences suggest different affinities to the platelet membrane.
Databáze:	OpenAIRE
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