PMID: 109614Jul 1, 1979

Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation

Journal of Medicinal Chemistry
D L VentonG C Le Breton

Abstract

A series of 13-azaprostanoic acids (4a-h) and a 15-azaprostanoic acid (11a) have been prepared. Synthesis of the 15-aza derivative is based on a novel transformation of a ketone to an N-substituted ethylenamine using a formylmethylimino phosphate derivative. Several of the azaprostanoic acid derivatives were found to be potent inhibitors of platelet aggregation induced by arachidonic acid, whereas no effect was observed on ADP-induced primary aggregation, indicating blockade of the platelet arachidonic acid cascade. The compounds do not inhibit bovine cyclooxygenase activity and are postulated as acting beyond the synthesis of the prostaglandin endoperoxides. The inhibitory effect of the 13-aza series is highly sensitive to both stereochemistry and length of the amino side chain. Any deviation from the natural prostaglandin skeletal arrangement results in decreased biological activity.

Citations

Sep 1, 1991·Medicinal Research Reviews·S E Hall
Jan 1, 1989·Progress in Lipid Research·H AritaK Hanasaki
Aug 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·G C Le BretonP V Halushka
Feb 1, 1986·The Journal of Clinical Investigation·D J FitzgeraldG A FitzGerald
Dec 15, 1982·Thrombosis Research·L V PariseG C Le Breton
Jan 22, 1992·Biochemical Pharmacology·S O KimG C Le Breton
Aug 1, 1986·British Journal of Pharmacology·S Hamid-Bloomfield, B J Whittle

Related Concepts

Magnesium ADP
Eicosatetraenoic Acids
Bos indicus
Saturated Fat
Platelet Aggregation
Prostanoic Acids
Seminal Vesicles
Structure-Activity Relationship
Cyclooxygenase Inhibitors

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