Syntheses and Adrenergic Activities of Ring-Fluorinated Epinephrines

Article abstract of DOI:10.1021/jm00118a019

The study of chemical and biological effects of fluorine substitution on the aromatic ring of catecholamines has now been extended to epinephrine (Epi). 2- and 6-fluoroepinephrines (2-FEpi and 6-FEpi) have been synthesized.Fluorine substitution on the 2- or 6-carbon of the aromatic ring alters the selectivity of epinephrine toward α- and β-adrenergic receptors, similar in manner to the change in selectivity seen with norepinephrine (NE).Thus, 2-FEpi is a relatively selective β-adrenergic ligand, while 6-FEpi is a relatively selective α-adrenergic ligand.Fluorine substitution of Epi also can markedly increase potency at either α- or β-adrenergic receptors.