Conversion of ergolines to hexahydro- and octahydrobenzo[f]quinolines (depyrroloergolines).
A general method has been developed for removal of the pyrrole ring from the ergolines. Oxidation of various ergolines at the 2,3 double bond gave formamido ketones 10, which afforded the amino ketones 11. These were deaminated to give the ketones 12, from which the carbonyl group was removed by reduction. The resulting depyrroloergolines (9) have, in contrast to the ergolines, little or no dopamine agonist activity in two tests.
D000818:Animals; D004298:Dopamine / Q000502:physiology; D004873:Ergolines / Q000494:pharmacology*; D006801:Humans; D008297:Male; D011388:Prolactin / Q000097:blood; D011758:Pyrroles; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013239:Stereotyped Behavior / Q000187:drug effects; D013329:Structure-Activity Relationship
D004873:Ergolines; D011758:Pyrroles; D011804:Quinolines; D011388:Prolactin; D004298:Dopamine