Format

Send to

Choose Destination
J Med Chem. 1988 Oct;31(10):1972-7.

Syntheses and adrenergic activities of ring-fluorinated epinephrines.

Author information

1
Laboratory of Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, Bethesda, Maryland 20892.

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.

PMID:
2845082
DOI:
10.1021/jm00118a019
[Indexed for MEDLINE]

Supplemental Content

Loading ...
Support Center