| Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines. | |
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MedLine Citation:
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PMID: 3989816 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles 3 or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes 4. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe less than NH2 less than OH, H less than NHOMe. On the other hand, in the tetrazole series, 2-unsubstituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress. |
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Authors:
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A Nohara; T Ishiguro; K Ukawa; H Sugihara; Y Maki; Y Sanno |
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Publication Detail:
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Type: In Vitro; Journal Article |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 28 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1985 May |
Date Detail:
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Created Date: 1985-06-03 Completed Date: 1985-06-03 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 559-68 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Benzopyrans / chemical synthesis*, pharmacology Guinea Pigs Hypersensitivity / drug therapy* Lung / drug effects, immunology Male Muscle Contraction / drug effects Muscle, Smooth / drug effects Passive Cutaneous Anaphylaxis / drug effects* Pyridines / chemical synthesis, pharmacology Rats Rats, Inbred Strains SRS-A / antagonists & inhibitors, biosynthesis Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Benzopyrans; 0/Pyridines; 0/SRS-A |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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