Antianaphylactic agents. 4. Synthesis and structure-activity relations of 3-(4-oxo-4H-1-benzopyran-3)acrylic acids, a new series of antiallergic substances, and some related compounds

Nohara, Akira; Kuriki, Hisashi; Saijo, Taketoshi; Ukawa, Kiyoshi; Murata, Tomoya; Kanno, Morio; Sanno, Yasushi

doi:10.1021/jm00235a008

Cited by 58 publications

(21 citation statements)

References 4 publications

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“…2.22) have been also described as an important motif for the development of antihistaminic compounds with additional antagonistic activity against LTD4 [157] . Chromone derivatives were also described as potential anti-asthmatic and antiallergic compounds by targeting mast cells and preventing the release of anaphylactic substances, such as the slow-reacting substance of anaphylaxis (SRS-A) [158] , or stopping the allergic responses triggered by them, by the inhibition of the passive cutaneous anaphylactic (PCA) reaction [159][160][161][162][163][164][165][166][167][168][169] .…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Chromone: A Valid Scaffold in Medicinal Chemistry

et al. 2014

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The last few decades have provided stunning progresses in the understanding of physiopathology of several diseases. The remarkable progress in research fields, like genetics, immunology, neurobiology, among others, as well as the advent of more powerful tools, have made it possible to characterize, monitor, and understand far more of the basis of physiology and disease. However, for some diseases the treatment remains a problematic issue as the efforts performed so far were not translated into therapeutic solutions. Notwithstanding the steady increase in the total amount of FCUP

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Section: Anti-inflammatory Activitymentioning

confidence: 99%

Chromone: A Valid Scaffold in Medicinal Chemistry

et al. 2014

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“…In recent years, baicalein having the same chromone structure as DSCG, which is the aglycone of baicalin present in Scutellaria baicalensis Georg, and its water-soluble derivative, disodium baicalein-6-phosphate have been found to inhibit allergic reactions in experimental models (6). In our continued research to develop a more potent orally effective antiallergic agent, a number of chromone derivatives were synthesized and tested biologically (7,8). One of these derivatives, 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344) was found to be highly effective, when given orally, in inhibiting passive cutaneous anaphylaxis (PCA) after a 72-hr latent period in rats.…”

mentioning

confidence: 99%

Antiallergic action of 6-ethyl-3-(1h-tetrazol-5-yl) chromone (aa-344) on immediate hypersensitivity reaction in rats

Kuriki

Saijo

Maki

et al. 1979

Japanese Journal of Pharmacology

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Abstract-A newly synthesized compound, 6-ethyl-3-(IH-tetrazol-5-yl)chromone (AA-344) given intravenously or orally inhibited considerably the 72-hr passive cutaneous anaphylaxis (72-hr PCA) induced by IgE in rats. The antiallergic action of AA-344 was neither due to the antihistamine or antiserotonin effect nor was it mediated via adrenergic mechanisms.The results obtained in a double sensitization with two IgE antibodies suggest that AA-344 may not impair antigen-antibody combi nation but probably prevents the release of chemical mediators including histamine. This assumption was supported by observation that AA-344 inhibited a reduction in the skin histamine content caused by the 72-hr PCA, without effect on the compound 48/80-induced histamine reduction. AA-344 also partially inhibited the IgGa-mediated 3-hr PCA in rats. These results indicate that the inhibitory action of AA-344 on the immediate hypersensitivity reactions is due to prevention of the release of chemical mediators from the mast cells, by acting on some process in sequential events leading to the mediator release following antigen-antibody combination.

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“…It has been reported that chromone derivatives bearing an acidic groups at position 3 displayed antiallergic activities. 19,20 Thus, in the present work some analogous compounds containing the allyl moiety at position 8 were prepared. Reaction of the carbonitrile 9 with sodium azide in the presence of aluminum chloride in tetrahydrofuran afforded 8-allyl-3-(1H-tetrazol-5-yl)chromone 10.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactions of 8-allylchromone-3-carboxaldehyde

Ibrahim¹,

Allimony²,

Abdel‐Halim³

et al. 2010

Arkivoc

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8-Allylchromone derivatives 5-7, 10 and 11 were prepared starting from 8-allylchromone-3-carboxaldehyde 4. Basic rearrangement of oxime 8 and/or carbonitrile 9 gave 8-allyl-2-aminochromone-3-carboxaldehyde 12. Chromeno[2,3-b] pyridines 14-20 were prepared via the reaction of 12 with malononitrile, cyanoacetamide, ethyl cyanoacetate, phenylthioacetonitrile, ethyl acetoacetate, ethyl benzoylacetate and barbituric acid. Structures of the new products have been deduced from elemental analysis and spectral data (IR, 1 H NMR and mass spectra).

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Antianaphylactic agents. 4. Synthesis and structure-activity relations of 3-(4-oxo-4H-1-benzopyran-3)acrylic acids, a new series of antiallergic substances, and some related compounds

Cited by 58 publications

References 4 publications

Chromone: A Valid Scaffold in Medicinal Chemistry

Chromone: A Valid Scaffold in Medicinal Chemistry

Antiallergic action of 6-ethyl-3-(1h-tetrazol-5-yl) chromone (aa-344) on immediate hypersensitivity reaction in rats

Synthesis and reactions of 8-allylchromone-3-carboxaldehyde

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