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1. Synthesis of Tic-D-Phe Psi[CH2-CH2] isostere and its use in the development of melanocortin receptor agonists.

Author

Tian X, Chen X, Gan L, Hayes JC, Switzer AG, Solinsky MG, Ebetino FH, Wos JA, Pinney BB, Farmer JA, Crossdoersen D, and Sheldon RJ

Subjects
Alkylation, Dipeptides chemistry, Humans, Lactams chemistry, Ligands, Models, Molecular, Molecular Mimicry, Molecular Structure, Receptor, Melanocortin, Type 3 agonists, Stereoisomerism, Structure-Activity Relationship, Dipeptides chemical synthesis, Dipeptides metabolism, Phenylalanine chemistry, Receptor, Melanocortin, Type 4 agonists
Abstract

The first synthesis of Tic-D-Phe Psi[CH(2)-CH(2)] isostere is described, which features diastereoselective alkylation of the tricyclic lactam 14. The use of this novel dipeptide isostere in the development of melanocortin agonists has been demonstrated by the synthesis of peptidomimetic 7 and non-peptidic ligand 27. Both compounds displayed significant binding and agonist potency at the MC4R.

Published
2006
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