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J Med Chem. 2011 Mar 24;54(6):1903-13. doi: 10.1021/jm101542c. Epub 2011 Feb 25.

Aminothiazolomorphinans with mixed κ and μ opioid activity.

Author information

1
Alcohol & Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, Massachusetts 02478, United States.

Abstract

A series of N-substituted and N'-substituted aminothiazole-derived morphinans (5) were synthesized for expanding the structure-activity relationships of aminothiazolo-morphinans. Although their affinities were somewhat lower than their prototype aminothiazolo-N-cyclopropylmorphinan (3), 3-aminothiazole derivatives of cyclorphan (1) containing a primary amino group displayed high affinity and selectivity at the κ and μ opioid receptors. [(35)S]GTPγS binding assays showed that the aminothiazolomorphinans were κ agonists with mixed agonist and antagonist activity at the μ opioid receptor. These novel N'-monosubstituted aminothiazole-derived morphinans may be valuable for the development of drug abuse medications.

PMID:
21351746
PMCID:
PMC3068608
DOI:
10.1021/jm101542c
[Indexed for MEDLINE]
Free PMC Article

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