2-(Aminomethyl)phenols, a new class of saluretic agents. 3. Effects of functional group reorientation and modification.
A series of modified 2-(aminomethyl)phenols was synthesized and tested orally in rats for saluretic and diuretic effects. Intravenous dog data are included as supplementary material to show that the diuretic responses, or lack thereof, may be obtained in a second species. Reorientation of the 2-(aminomethyl) group either meta or para to the hydroxyl substituent resulted in loss of diuretic effects. Similarly, replacement of either the phenolic hydroxyl or the aminomethyl group with other functional moieties substantially diminished saluretic effects.
D000588:Amines / Q000138:chemical synthesis*; D000818:Animals; D001596:Benzylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004232:Diuretics / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009318:Natriuresis / Q000187:drug effects*; D051381:Rats; D013329:Structure-Activity Relationship
D000588:Amines; D001596:Benzylamines; D004232:Diuretics; C032416:2-(aminomethyl)phenol