Synthesis of fluorinated analogues of the neurosteroid GABA(A) receptor antagonist, 17-PA

Gildas Pascal Deniau, Keith T. Sillar, David O'Hagan

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


The steroid 17-PA is a GABA(A) receptor antagonist which is finding use as a tool in evaluating agonistic/antagonistic activity at GABA(A) receptors. Compounds with improved efficacy over 17-PA would be are advantageous for such studies. Accordingly a series of novel analogues of the neurosteroid 17-PA have been prepared and a convenient two-step route is presented which is amenable to the synthesis of analogues with electron-donating para-aromatic substituents including fluorine. However, for the metafluoro analogue then the original four-step route to 17-PA remains more efficient overall. The paper describes these syntheses and discusses the electronic factors which influence this synthetic chemistry. (c) 2008 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)881-887
Number of pages7
JournalJournal of Fluorine Chemistry
Publication statusPublished - Sept 2008


  • Neurosteroids
  • 17-PA
  • gamma-Aminobutyric acid receptors
  • Medicinal chemistry


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