Synthesis and Biological Activity of Analogues of β-Chlornaltrexamine and β-Funaltrexamine at Opioid Receptors

P. S. Portoghese, Michael D. Rein, A. E. Takemori

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Chlornaltrexamine and β-funaltrexamine analogues 4–7 with different length “arms” to which an electrophilic moiety is attached were synthesized in an effort to obtain affinity labels that would selectively and irreversibly block specific opioid receptor types and subtypes. One of the compounds, 4, was a potent, irreversible blocker of opioid receptors in the guinea pig ileum and mouse vas deferens preparations. The results of this study suggest that nucleophiles that are remote from the recognition locus are capable of alkylation by reactive electrophiles.

Original languageEnglish (US)
Pages (from-to)1861-1864
Number of pages4
JournalJournal of medicinal chemistry
Volume29
Issue number10
DOIs
StatePublished - Jan 1 1986

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