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  • Title: Ergot alkaloids. Synthesis of 6-methyl-8-ergolenes as inhibitors of prolactin release.
    Author: Li GS, Robinson JM, Floss HG, Cassady JM.
    Journal: J Med Chem; 1975 Sep; 18(9):892-5. PubMed ID: 1159711.
    Abstract:
    A general synthetic route from elymoclavine (4a) to a variety of C-17 substituted 8-ergolenes has been established. [The C-17 position is the carbon attached to C-8 of the ergoline (1) skeleton as indicated in structure 2.] This route involves displacement reactions on the allylic chloride (4h) prepared from 4a by reaction with thionyl chloride. Conversion of the naturally occurring tricyclic clavines, chanoclavine I (5a) and isochanoclavine I (5b), to the tetracyclic clavine, agroclavine (4i), has been achieved. The new compounds prepared were tested for prolactin-inhibiting ability and were found to possess activity. One of the compounds prepared, 6-methyl-8-ergolenylacetamide (4k), was very potent, comparing favorably in activity to the best prolactin inhibitors reported to date.
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