Synthesis and pharmacology of trans-4-n-propyl-3,4,4a,10b-tetrahydro-2H,5H-1-benzopyrano[4,3-b]1,4-oxazin-7- and -9-ols. The significance of nitrogen pka values for central dopamine receptor activation

Durk Dijkstra*, Theo B. A. Mulder, Hans Rollema, Pieter G. Tepper, Jan Van der Weide, Alan S. Horn

*Corresponding author for this work

    Research output: Contribution to journalArticleAcademicpeer-review

    30 Citations (Scopus)

    Abstract

    The 6-oxa analogues of potent dopamine agonists, hexahydronaphthoxazines (4a,4b), have been tested for dopamine receptor binding and stimulating activity and were found to be almost inactive. pKa value determinations indicated that these compounds are protonated to approximately 2%, while potent compounds are protonated to a much greater extent. These results strongly support the assumption that the protonated form of DA agonists is the active species at the receptor.
    Original languageEnglish
    Pages (from-to)2178-2182
    Number of pages5
    JournalJournal of Medicinal Chemistry
    Volume31
    Issue number11
    DOIs
    Publication statusPublished - Nov-1988

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