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Mazur, A.W. et al.

Mazur, Kulesza, Mishra, Cross-Doersen, Russell, Ebetino,

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

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 the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R. Thus, the 2,4,6-trisubstituted tetrahydropyran scaffold has provided a potentially useful peptidomimetic lead, and conceptual cyclization of peptide moieties can offer a valuable design strategy in peptidomimetic research.[1]

References

Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors. Mazur, A.W., Kulesza, A., Mishra, R.K., Cross-Doersen, D., Russell, A.F., Ebetino, F.H. Bioorg. Med. Chem. (2003) [Pubmed]

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