199940-76-6Relevant articles and documents
Investigation of the 4-O-alkylamine substituent of non-peptide quinolone GnRH receptor antagonists
DeVita, Robert J.,Goulet, Mark T.,Wyvratt, Matthew J.,Fisher, Michael H.,Lo, Jane-L,Yang, Yi Tien,Cheng, Kang,Smith, Roy G.
, p. 2621 - 2624 (1999)
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.
