Antiallergic activity of 2-phenyl-8-azapurin-6-ones

The synthesis and antiallergic activity in the rat passive cutaneous anaphylactic reaction of a series of 2-phenyl-8-azapurin-6-ones are described. Early in the investigation, a linear free-energy equation was established in which the activity was related to the size and hydrogen bonding capacity of...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-11, Vol.18 (11), p.1117-1122
Main Authors: Broughton, B. J, Chaplen, P, Knowles, P, Lunt, E, Marshall, S. M, Pain, D. L, Wooldridge, K. R. H
Format: Article
Language:English
Subjects:
Animals
Aza Compounds - chemical synthesis
Aza Compounds - pharmacology
Cromolyn Sodium - pharmacology
Hypersensitivity - drug therapy
Male
Passive Cutaneous Anaphylaxis - drug effects
Purinones - chemical synthesis
Purinones - pharmacology
Rats
Skin Tests
Structure-Activity Relationship
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Summary:The synthesis and antiallergic activity in the rat passive cutaneous anaphylactic reaction of a series of 2-phenyl-8-azapurin-6-ones are described. Early in the investigation, a linear free-energy equation was established in which the activity was related to the size and hydrogen bonding capacity of the ortho substituent in the phenyl ring. This relationship was used to provide guidance and limits for subsequent work leading to 2-o-propoxyphenyl-8-azapurin-6-one which is 40 times more potent than disodium cromoglycate. It is suggested that good antiallergic activity in this series is associated with coplanarity of the phenyl group with the azapurin-6-one which would be favored by a high degree of hydrogen bonding.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00245a014