Investigation of Phenolic Bioisosterism in Opiates: 3-Sulfonamido Analogues of Naltrexone and Oxymorphone
- 15 February 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (6) , 819-821
- https://doi.org/10.1021/ol005561+
Abstract
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.Keywords
This publication has 5 references indexed in Scilit:
- 8-Aminocyclazocine analogues: synthesis and structure–activity relationshipsBioorganic & Medicinal Chemistry Letters, 2000
- Rational Development of Practical Catalysts for Aromatic Carbon−Nitrogen Bond FormationAccounts of Chemical Research, 1998
- Substituted (Pyridylmethoxy)naphthalenes as Potent and Orally Active 5-Lipoxygenase Inhibitors: Synthesis, Biological Profile, and Pharmacokinetics of L-739,010Journal of Medicinal Chemistry, 1997
- A new example of a morphine‐sensitive neuro‐effector junction: adrenergic transmission in the mouse vas deferensBritish Journal of Pharmacology, 1972
- Analysis of Dried Blood Plasma by Spark Source Mass SpectrometryNature, 1964