2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists. 2. Synthesis, chirality, and pharmacokinetics.

@article{Borthwick200525diketopiperazinesAP,
  title={2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists. 2. Synthesis, chirality, and pharmacokinetics.},
  author={Alan D. Borthwick and Dave E Davies and Anne M. Exall and David George Hubert Livermore and Steve L Sollis and Fabrizio Nerozzi and Michael James Allen and Marion J. Perren and Shalia S Shabbir and Patrick M Woollard and Paul G Wyatt},
  journal={Journal of medicinal chemistry},
  year={2005},
  volume={48 22},
  pages={
          6956-69
        }
}
A short stereoselective synthesis of a series of chiral 7-aryl-2,5-diketopiperazines oxytocin antagonists is described. Varying the functionality and substitution pattern of substituents in the 7-aryl ring and varying the chirality of this exocyclic ring have produced potent oxytocin antagonists (pK(i) > 8.5). SAR and pharmacokinetic profiling of this series of (3R,6R,7R)-2,5-diketopiperazines together with the introduction of an ortho F group in the 7-aryl ring to improve rat pK has culminated… CONTINUE READING
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