title: (Acylaryloxy)acetic acid diuretics. 1. (2-Alkyl- and 2,2-dialkyl-1-oxo-5-indanyloxy)acetic acids.
abstract: The discovery of the (acryloylaryloxy)acetic acids as a new class of potent diuretics prompted the investigation of related bicyclic compounds. Annelated analogues of the parent series, the (2-alkyl- and 2,2-dialkyl-1-oxo-5-indanyloxy)acetic acids, were the subjects of this study. Those compounds, unlike the monocyclic parent compound, lacked the double bond adjacent to the carbonyl group. More importantly, they possessed both saluretic and uricosuric properties. The optimal single 2-substituents for maximal saluretic and uricosuric activity were determined. In general, better activity was observed when a second 2-alkyl substituent (especially methyl) was present in the molecule. Replacement of the carboxy substituent by 5-tetrazolyl generally resulted in a reduction in activity.
mesh_terms: D000085:Acetates / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology; D000284:Administration, Oral; D000818:Animals; D004231:Diuresis / Q000187:drug effects; D004232:Diuretics / Q000008:administration & dosage / Q000138:chemical synthesis*; D004285:Dogs; D005260:Female; D007189:Indans / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D007275:Injections, Intravenous; D008297:Male; D009318:Natriuresis / Q000187:drug effects; D002679:Pan troglodytes; D051381:Rats; D012964:Sodium / Q000652:urine; D013329:Structure-Activity Relationship; D014528:Uricosuric Agents / Q000008:administration & dosage / Q000138:chemical synthesis
chemical_list: D000085:Acetates; D004232:Diuretics; D007189:Indans; D014528:Uricosuric Agents; D012964:Sodium