ABSTRACT
Some benzothienoquinolinecarboxylic acids were synthesized and tested in the rat passive cutaneous anaphylaxis (PCA) assay as potential antiallergic agents. Many of the compounds showed activity comparable to that shown by disodium cromoglycate (DSFG); two of them, 1,4-dihydro-4,6,6-trioxo-5-chloro[1]benzothieno[2,3-g]quinoline-2-carboxylic acid and 1,4-dihydro-1,7-dioxo[1]benzothieno[3,2-f]quinoline-3-carboxylic acid, showed potency approximately eightfold greater than that of DSCG in the PCA assay.
Subject(s)
Passive Cutaneous Anaphylaxis/drug effects , Quinolines/chemical synthesis , Animals , Carboxylic Acids/chemical synthesis , Carboxylic Acids/pharmacology , Cromolyn Sodium/pharmacology , Quinolines/pharmacology , Rats , Structure-Activity RelationshipABSTRACT
Substitution of 1,4-dihydro-4-oxoquinoline-2-carboxylic acid by acetyl, benzoyl, and phenylsulfonyl substituents was found to enhance activity in the rat passive cutaneous anaphylaxis assay. A further increase in activity, to equipotency with DSCG, was achieved by incorporation of the 8-benzoyl moiety into a tetracyclic structure to give 1,4-dihydro-4,11(1H,11H)-dioxoindeno[1,2-h]quinoline-2-carboxylic acid (20). In contrast, the reverse isomer 19 was found to have little activity.