Synthesis and antiallergic activity of 2-hydroxy-3-nitro-1,4-naphthoquinones

A selection of novel 2-hydroxy-3-nitro-1,4-naphthoquinones are shown to be potent inhibitors of rat passive cutaneous anaphylaxis (PCA) and to have highest potency with alkyl substitution at both C-6 and C-7. The most potent compounds were 7c and 7e which produced a 50% inhibition in the rat PCA tes...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1977-08, Vol.20 (8), p.1059-1064
Main Authors: Buckle, Derek R, Cantello, Barrie C. C, Smith, Harry, Smith, Raymond J, Spicer, Barbara A
Format: Article
Language:English
Subjects:
Animals
Depression, Chemical
Male
Naphthoquinones - chemical synthesis
Naphthoquinones - pharmacology
Passive Cutaneous Anaphylaxis - drug effects
Rats
Structure-Activity Relationship
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Summary:A selection of novel 2-hydroxy-3-nitro-1,4-naphthoquinones are shown to be potent inhibitors of rat passive cutaneous anaphylaxis (PCA) and to have highest potency with alkyl substitution at both C-6 and C-7. The most potent compounds were 7c and 7e which produced a 50% inhibition in the rat PCA test at doses of about 10 micrometerM/kg following subcutaneous administration and showed activity after oral administration. Related 4-hydroxy-3-nitro-2(1H)-naphthalenones had no effect on rat PCA in doses up to 500 micrometerM/kg.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00218a014