Synthesis of Tic-d-Phe Ψ[CH2–CH2] isostere and its use in the development of melanocortin receptor agonists

Autor:	Beth B. Pinney, Jeffery C. Hayes, Xinrong Tian, Russell James Sheldon, Mark Gregory Solinsky, Adrian Gregory Switzer, Frank H. Ebetino, Doreen Crossdoersen, John August Wos, Julie A. Farmer, Xuemei Chen, Lixian Gan
Rok vydání:	2006
Předmět:	Models Molecular Agonist Alkylation Lactams medicine.drug_class Stereochemistry Isostere Peptidomimetic Phenylalanine Clinical Biochemistry Pharmaceutical Science Ligands Biochemistry Chemical synthesis Structure-Activity Relationship chemistry.chemical_compound Melanocortin receptor Drug Discovery medicine Humans Molecular Biology Dipeptide Molecular Structure Chemistry Molecular Mimicry Organic Chemistry Stereoisomerism Dipeptides Combinatorial chemistry Lactam Receptor Melanocortin Type 4 Molecular Medicine Melanocortin Receptor Melanocortin Type 3
Zdroj:	Bioorganic & Medicinal Chemistry Letters. 16:1721-1725
ISSN:	0960-894X
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::29f2e272b4df8d3a15260f691f187f61 https://doi.org/10.1016/j.bmcl.2005.12.005 Zobrazit plný text záznamu Full Text from ScienceDirect