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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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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container_end_page 1064
container_issue 8
container_start_page 1059
container_title Journal of medicinal chemistry
container_volume 20
creator Buckle, Derek R
Cantello, Barrie C. C
Smith, Harry
Smith, Raymond J
Spicer, Barbara A
description 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.
doi_str_mv 10.1021/jm00218a014
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source ACS CRKN Legacy Archives
subjects Animals
Depression, Chemical
Male
Naphthoquinones - chemical synthesis
Naphthoquinones - pharmacology
Passive Cutaneous Anaphylaxis - drug effects
Rats
Structure-Activity Relationship
title Synthesis and antiallergic activity of 2-hydroxy-3-nitro-1,4-naphthoquinones
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