[Synthesis and antiaggregation activity of prostacyclin analogs. II. Direct synthesis of 15-fluoro-13,14-didehydrocarbacyclin].
E- and Z-isomers of 15-fluoro-13,14-dehydrocarbacyclin were synthesized starting from 2,3-epoxy-bicyclo[3.3.0]octan-6-one ethylene ketal with the use of 3-fluoro-1-octynydlithium.BF3 reagent and Wittig condensation. The ratio of isomeric the oxirane opening reaction and Wittig olefinization products was in each case 1:1. The synthesized compounds were identified by 13C NMR spectra. The antiaggregating activity of 5E-isomer was 2 x 10(-4) of the activity of corresponding 15-hydroxy compound, 5Z-isomer being even less active.
Lopp
M I
MI
Bergmann
M A
MA
Bezuglov
V V
VV
Vialimiaé
T K
TK
Lopp
A Kh
AKh
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D011464:Epoprostenol / Q000138:chemical synthesis* / Q000494:pharmacology / Q000031:analogs & derivatives; D066298:In Vitro Techniques; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis*; D011465:Prostaglandins, Synthetic / Q000494:pharmacology; D011817:Rabbits
D010975:Platelet Aggregation Inhibitors; D011465:Prostaglandins, Synthetic; C057736:15-fluoro-13,14-dehydrocarbacyclin; D011464:Epoprostenol
Sintez i antiagregatsionnaia aktivnost' analogov prostatsiklina. II. Priamoĭ sintez 15-ftor-13,14-didegidrokarbatsiklina.