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A new series of 1,2,3-trisubstituted-2-propen-1-one derivatives (9a-v, 10a-j, 13a-c, 14a-j) and 3,4-disubstituted-4-oxo-2-butenoic acids (6a-i, 7a-n) with azole compounds were synthesized. Inhibitory activities against rat passive cutaneous anaphylaxis (PCA) reaction and histamine release from rat mast cells were tested. The ester derivatives (7a-n, 14a-j) exhibited a more potent inhibitory activity against histamine release compared with alkylamine (9a-v), beta-hydroxyethoxy (10a-j) and carboxylic acid (6a-i, 13a-c) derivatives, but somewhat weaker in their anti-PCA activity. Structure-activity relationships were discussed.

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Studies on Anti-allergic Agent. I. 1, 2, 3-Trisubstituted-2-propen-1-one Derivatives, 3, 4-Disubstituted-4-oxo-2-butenoic Acids and the Related Compounds