European Journal of Medicinal Chemistry p. 155 - 159 (1992)
Update date:2022-07-31
Topics:
Lopp
Kobzar
Bergmann
Pehk
Lopp
Valimae
Viigimaa
Lille
Novel stable bicyclo[3.3.0]octanic and bicyclo[4.2.0]octanic 13,14-didehydrocarbacyclins 1a-c, 2a bearing an achiral cyclohexanoic group at C-14 were synthesized. These analogues have been characterized by 13C NMR spectroscopy. Compounds 1a-c and 2a were tested on rabbit and human platelet-rich blood plasma and 1a-c on rat stomach and guinea pig trachea smooth muscles. E-isomers of 1a-b were found to be less active but more selective than PGE1. The anti-aggregative potency of E-isomer of compounds 1a-b and Z-isomer of 2a on human platelets was 10-1-10-2 of the activity of PGE1. The contractive activity of bicyclo[3.3.0]octane analogues 1a-c was 10-3-10-4 of that for PGE1. On platelets and guinea-pig trachea 5E-isomers of the corresponding analogues were more potent, whereas on rat stomach muscle 5Z-isomers were.
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