Bioorganic and Medicinal Chemistry Letters p. 2621 - 2624 (1999)
Update date:2022-08-05
Topics:
DeVita, Robert J.
Goulet, Mark T.
Wyvratt, Matthew J.
Fisher, Michael H.
Lo, Jane-L
Yang, Yi Tien
Cheng, Kang
Smith, Roy G.
Synthesis and in vitro activity of the enantiomers of quinolone GnRH antagonist (±)-1 are reported. Chiral amino alcohols were prepared from the appropriate cyclic D- or L-amino acids by the Arndt-Eistert homologation followed by reduction of the resulting esters. Incorporation of these pharmacophores was achieved via a novel Mitsunobu alkylation of 4-hydroxyquinolones. The key amine pharmacophore for binding to the rat GnRH receptor was most active in the S-configuration. Ring size was not important for potency with 4, 5, 6, and 7-membered ring amines exhibiting similar potency.
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