| Popis: |
By the reaction of 3-(3′-acetoxyoctyl)-2-(6′-carboxyhexyl)-2-cyclopenten-1-one, the acetoxy derivative of Prostaglandin E1 - 237 (PGE1 - 237), with N-bromosuccinimide in carbon tetrachloride, followed by treatment of the reaction product with silver acetate in acetic acid, an acetoxy group was introduced at the allyl position of the ring. After hydrolysis of both acetoxy groups, 2-(6′-carboxyhexyl)-4-hydroxy-3-(3′-hydroxyoctyl)-2-cyclopenten-1-one was obtained. In an attempt to convert the latter into 2-(6′-carboxyhexyl)-4-hydroxy-3-(3′-hydroxyoctyl)-1-cyclopentanone (racemic dihydro-PGE1), hydrogenation with a 5 % rhodium on carbon catalyst was carried out. Both reduction of the double bond in the ring and hydrogenolysis of the hydroxy group attached to the ring occurred, leading to 2-(6′-carboxyhexyl)-3-(3′-hydroxyoctyl)-1-cyclo-pentanone. However, racemic dihydro-PGE1 was also obtained in low yield. It showed some biological activity on blood-platelet aggregation. |
