Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors.

@article{Mazur2003NovelTP,
  title={Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors.},
  author={Adam W. Mazur and Anna Kulesza and Rajesh Kumar Mishra and Doreen Cross-Doersen and Anne Russell and Frank H. Ebetino},
  journal={Bioorganic & medicinal chemistry},
  year={2003},
  volume={11 14},
  pages={3053-63}
}
We have prepared novel peptidomimetics based on a 2,4,6-trisubstituted tetrahydropyran. This scaffold was constructed in an isosteric transformation using conceptual constraints imposed on a tripeptide moiety involving O(i)'-C(i+1)(gamma) and O(i)'-N(i+2) formal cyclization modes. A series of regioselective transformations commencing with a substituted dihydropyran-4-one readily provided the required analogues. Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of… CONTINUE READING