[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].
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.
Hirao
H
H
Shikoku Chemical Co., Ltd., Tokushima, Japan.
Fujita
T
T
Iwasaki
Y
Y
Ide
H
H
Inoue
S
S
Kitagawa
K
K
Futaki
S
S
Kawanishi
H
H
Akita
T
T
D000818:Animals; D003864:Depression, Chemical; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000494:pharmacology; D006636:Histamine Release / Q000187:drug effects*; D007651:Keto Acids / Q000138:chemical synthesis / Q000494:pharmacology; D007659:Ketones / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D010323:Passive Cutaneous Anaphylaxis / Q000187:drug effects*; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D005229:Fatty Acids, Monounsaturated; D007651:Keto Acids; D007659:Ketones