Importance of carbon 6 chirality in conferring irreversible opioid antagonism to naltrexone-derived affinity labels

…, DS Fries, AE Takemori, PS Portoghese

Index: Sayre; Larson; Fries; Takemori; Portoghese Journal of Medicinal Chemistry, 1983 , vol. 26, # 9 p. 1229 - 1235

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Citation Number: 49

Abstract

A series of five epimeric pairs of naltrexone derivatives that contain an electrophilic substituent at the 601-or 6P-position was synthesized and tested on the guinea pig ileal longitudinal muscle (GPI) and mouse vas deferens (MVD) preparations in order to determine if the orientation of the electrophile is important for covalent bonding to opioid receptors. In the GPI all compounds were pharmacologically active as reversible agonists, but only the ...