Investigation of phenolic bioisosterism in opiates

3-sulfonamido analogues of naltrexone and oxymorphone

Christopher R. McCurdy, Robert M. Jones, Philip S. Portoghese

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

formula presented The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. On the basis of its putative role as a hydrogen-bonding donor in the interaction with opioid receptors, it was replaced with a sulfonamide group because of their similar pKa values. The first thebaine-derived 3-amino (8a, 8b) and subsequent sulfonamide analogues (10a, 10b) were synthesized from naltrexone (1a) and oxymorphone (1b) in a linear nine-step synthesis. The sulfonamides were tested in vitro and found inactive.

Original languageEnglish (US)
Pages (from-to)819-821
Number of pages3
JournalOrganic Letters
Volume2
Issue number6
StatePublished - Mar 23 2000

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Opiate Alkaloids
Oxymorphone
Naltrexone
Sulfonamides
analogs
Thebaine
activity (biology)
Opioid Receptors
Hydrogen Bonding
Bioactivity
ligands
Hydrogen bonds
hydrogen
synthesis
Ligands
interactions

Cite this

Investigation of phenolic bioisosterism in opiates : 3-sulfonamido analogues of naltrexone and oxymorphone. / McCurdy, Christopher R.; Jones, Robert M.; Portoghese, Philip S.

In: Organic Letters, Vol. 2, No. 6, 23.03.2000, p. 819-821.

Research output: Contribution to journalArticle

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