Benzopyrones. 14. Synthesis and antiallergic properties of some N-tetrazolylcarboxamides and related compounds.
A series of chromones containing an acidic group has been synthesized and screened for the ability to inhibit passive cutaneous anaphylaxis and the release of histamine from mast cells of the rat. Many of the chromones contain the N-(5-tetrazolyl)carboxamido group, a novel source of acidity. Others contain a carboxyl, C-(5-tetrazolyl), 5-(4H)-oxotetrazolinyl, or N-(5-tetrazolyl)sulfonamido function. The compounds were compared with cromolyn sodium (sodium cromoglycate) and many were found to be powerful inhibitors of anaphylaxis. The most potent was 7-methoxy-4-oxo-N-(5-tetrazolyl)-4H-1-benzopyran-2-carboxamide (15). Structure-activity relationships among the chromones and also some related compounds are discussed.
D000707:Anaphylaxis / Q000378:metabolism; D000818:Animals; D001393:Azoles / Q000138:chemical synthesis*; D002867:Chromones / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D006636:Histamine Release / Q000187:drug effects; D006801:Humans; D006967:Hypersensitivity / Q000188:drug therapy*; D066298:In Vitro Techniques; D008168:Lung / Q000187:drug effects / Q000378:metabolism; D008297:Male; D008407:Mast Cells / Q000187:drug effects / Q000378:metabolism; D010323:Passive Cutaneous Anaphylaxis / Q000187:drug effects; D051381:Rats; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D001393:Azoles; D002867:Chromones; D013777:Tetrazoles