Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: A new series of hybrid molecules with significant binding affinity for μ-opioid receptors and I2-imidazoline binding sites

摘要

A new series of fentanyl derivatives [i.e., N-[1-(2-phenethyl)-4-piperidyl] -N-(guanidinoalkyl)propanamide] bearing aliphatic alkaneguanidinium moieties were prepared. Their affinities for the μ opioid receptors and for the I 2-imidazoline binding sites (I2-IBS) were determined on human post-mortem prefrontal cortex membranes. All of these hybrid compounds had significant and/or very high affinity for both receptors in the nanomolar range, meaning an improvement compared to the prototype N-[1-(2-phenethyl)-4- piperidyl]-N-(guanidinopropyl)propanamide previously reported. © 2003 Elsevier Ltd. All rights reserved.