Syntheses and adrenergic activities of ring-fluorinated epinephrines

Publisher Website
Google Scholar
Abstract
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 .alpha.- and .beta.-adrenergic receptors, similar in manner to the change in selectivity seen with norepinephrine (NE). Thus, 2-FEpi is a relatively selective .beta.-adrenergic, ligand, while 6-FEpi is a relatively selective .alpha.-adrenergic ligand. Fluorine substitution of Epi also can markedly increase potency at either .alpha.- or .beta.-adrenergic receptors.