(Vinylaryloxy)acetic acids. A new class of diuretic agents. 3. ((2-Nitro-1-alkenyl)aryloxy)acetic acids.
A series of [(2-nitro-1-alkenyl)aryloxy]acetic acids was synthesized and tested in dogs for saluretic and diuretic activity. A number of these compounds exhibit a high order of activity on iv or po administration; representative of these is (E)-[2,3-dichloro-4-(2-nitropropenyl)phenoxy]acetic acid (5). The most highly active compounds are qualitatively similar in action to [2,3-dichloro-4-(2-methylenebutyryl)phenoxylacetic acid  (ethacrynic acid) in causing a prompt increase in the excretion of water and of sodium and chloride ions in approximately equimolar amounts but are three to five times as potent. Potassium ion excretion is increased  but less markedly than sodium excretion.
D000085:Acetates / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology; D000284:Administration, Oral; D000475:Alkenes / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D002712:Chlorides / Q000652:urine; D004231:Diuresis / Q000187:drug effects; D004232:Diuretics / Q000008:administration & dosage / Q000138:chemical synthesis*; D004285:Dogs; D007275:Injections, Intravenous; D009318:Natriuresis / Q000187:drug effects; D011188:Potassium / Q000652:urine; D012964:Sodium / Q000652:urine; D013329:Structure-Activity Relationship
D000085:Acetates; D000475:Alkenes; D002712:Chlorides; D004232:Diuretics; D012964:Sodium; D011188:Potassium