Agents acting on the central nervous system. XII. 3-t-aminopropiophenones as central muscle relaxants and diuretics

Abstract

The syntheses and pharmacological evaluation of a series of 2- and 3-l-aminopropiophenones and of certain 3-and 4-l-aminobutyrophenones, 2-l-aminoethyl aryl sulfoxides and sulfones, 3-l-amino-1-(4-pyridyl)propan-1-one, and 3-t-aminoindan-1-one are presented. The 3-l-aminopropiophenones have been found to possess diverse types of biological activities, which include central depressant, adrenergic receptor blocking, central muscle relaxant, local anesthetic, diuretic, antifungal, and antiviral activities; and their structure-activity relationships are discussed. 4′-Fluoro-3-(1-piperidyl)propiophenone (1) has powerful central muscle relaxant activity, being twice as effective as mephenesin; 2′,4′-dimethyl-3-(4-morpholinyl)propiophenone (17) is diuretic and 4′-fluoro-3-(4-morpholinyl)propiophenone (5) is antifungal.