Synthesis and antiinflammatory activity of some 1,6-methano[10]annuleneacetic acids

Some new approaches to the 1,6-methano[10]annulene system are described. The routes were used to prepare 1,6-methano[10]annulene-3-acetic acid and the alpha-methyl analog. The compounds showed antinflammatory and analgesic activity, though less than that of corresponding naphthalene compounds; the p...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-06, Vol.18 (6), p.583-586
Main Authors: Nelson, P. H, Bartsch, G. A, Untch, K. G, Fried, J. H
Format: Article
Language:English
Subjects:
Acetates - chemical synthesis
Acetates - therapeutic use
Animals
Anti-Inflammatory Agents - chemical synthesis
Anti-Inflammatory Agents - therapeutic use
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - therapeutic use
Aspirin - therapeutic use
Bridged-Ring Compounds - chemical synthesis
Bridged-Ring Compounds - therapeutic use
Carrageenan
Edema - chemically induced
Edema - drug therapy
Mice
Phenylbutazone - therapeutic use
Rats
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Description
Summary:Some new approaches to the 1,6-methano[10]annulene system are described. The routes were used to prepare 1,6-methano[10]annulene-3-acetic acid and the alpha-methyl analog. The compounds showed antinflammatory and analgesic activity, though less than that of corresponding naphthalene compounds; the possible effect of the chirality of the annulene on the observed biological activity is discussed.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00240a012