Ergot alkaloids. Synthesis of 6-alkyl-8-ergolenes and 6-methyl-8-aminoergolines as potential prolactin inhibitors.
The synthesis of several N-6 derivatives of elymoclavine (3) and potential alkylating derivatives of 6-methyl-8-aminoergolines (12) is described. These compounds were screened for prolactin-inhibiting ability and 6-propyl-8-hydroxymethyl-8-ergolene (9) was found to be as active as the most potent prolactin inhibitors reported to date. The total synthesis of racemic methyl dihydrolysergate I (23), having a trans C, D ring fusion, from the tricyclic ketone 18 is also described.
D000818:Animals; D004873:Ergolines / Q000138:chemical synthesis* / Q000494:pharmacology; D004876:Ergot Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D008968:Molecular Conformation; D011388:Prolactin / Q000037:antagonists & inhibitors* / Q000097:blood; D051381:Rats; D013329:Structure-Activity Relationship
D004873:Ergolines; D004876:Ergot Alkaloids; D011388:Prolactin