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J Med Chem. 2003 Feb 27;46(5):677-80.

2,6-Dimethyltyrosine analogues of a stereodiversified ligand library: highly potent, selective, non-peptidic mu opioid receptor agonists.

Author information

1
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Abstract

We recently reported the use of an exhaustively stereodiversified library based on endomorphin-2 (1) to discover mu opioid receptor (MOR) ligands of type 2-4. Here, we report the synthesis and evaluation of 2,6-dimethyltyrosine analogues 5-10. These analogues showed improved affinity for MOR relative to 2-4. In the cases of 5 and 6, we synthesized and evaluated five stereoisomers of each, thereby discovering stereoisomers with unexpected potency, selectivity, and efficacy. These results illustrate the utility of acyclic, stereodiverse libraries.

PMID:
12593647
DOI:
10.1021/jm025608s
[Indexed for MEDLINE]

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