Synthesis of 13,14-dehydroprostacyclin methyl ester: a potent inhibitor of platelet aggregation.
AUTOR(ES)
Fried, J
RESUMO
The structure of the most recently discovered, biologically highly active prostaglandin, PGI2 or prostacyclin, is correctly predicted on biogenetic grounds, and a general synthesis starting with prostaglandins of the F2alpha series is reported. Starting with the biologically active 13,14-dehydro-PGF2alpha, the synthesis involves formation of a 5-bromo-6,9alpha-epoxy derivative, followed by esterification and dehydrobromination of the methyl ester to form the prostacyclin structure. The stereochemistry at C-5 and C-6 of all reported products is assigned on the basis of experimental findings and mechanistic reasoning. 13,14-Dehydroprostacyclin methyl ester is considerably more stable at pH 7.5 than prostacyclin. It inhibits platelet aggregation induced by a variety of agents and causes an increase in renal blood flow in the dog at nanomolar levels.
ACESSO AO ARTIGO
http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=432136Documentos Relacionados
- Coronary vasodilator activity of 13,14-dehydroprostacyclin methyl ester: comparison with prostacyclin and other prostanoids.
- Unusual pulmonary vasodilator activity of 13,14-dehydroprostacyclin methyl ester: comparison with endoperoxides and other prostanoids.
- Salivary gland extracts from the deerfly contain a potent inhibitor of platelet aggregation.
- Vascular relaxing activity and stability studies of 10,10-difluoro-13,14-dehydroprostacyclin.
- Agkistrodon piscivorus piscivorus platelet aggregation inhibitor: a potent inhibitor of platelet activation.