Identification of neutral 4-O-alkyl quinolone nonpeptide GnRH receptor antagonists

Robert J. DeVita, Mamta Parikh, Jinlong Jiang, Jason A. Fair, Jonathan R. Young, Thomas F. Walsh, Mark T. Goulet, Jane L. Lo, Ning Ren, Joel B. Yudkovitz, Jisong Cui, Yi T. Yang, Kang Cheng, Susan P. Rohrer, Matthew J. Wyvratt

Research output: Contribution to journalArticlepeer-review

13 Scopus citations


Potent neutral replacements of the basic amine at the 4-position of quinolone non-peptide GnRH antagonists are reported. A series of neutral, nonbasic quinolone GnRH antagonists were prepared via Mitsunobu alkylation of protected and unprotected 4-hydroxy quinolone intermediates. The synthetic route was improved by utilization of unique reactivity and convergency afforded by the use of mono and bis-trimethylsilylethyl protected quinolones. Potent neutral GnRH antagonists were identified, including ether and lactam derivatives, that show similar in vitro binding affinity and functional activity as compared to the earlier basic 4-aminoalkyl quinolone series of nonpeptide GnRH antagonists.

Original languageEnglish (US)
Pages (from-to)5599-5603
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Issue number22
StatePublished - Nov 15 2004
Externally publishedYes


  • Antagonist
  • GnRH
  • Quinolone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science


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