3,7-Diazabicyclane. A new narcotic analgesic

The synthesis of a series of 9-phenyl-3,7-diazabicyclanes and 9-(m-hydroxyphenyl)-3,7-diazabicyclanes is described. Members of both series were tested for antinociception in rat tail withdrawal and mouse acetic acid writhing assays. Their affinities for opiate receptors in rat brain homogenate were...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1986-10, Vol.29 (10), p.2111-2113
Main Authors: Salva, Paul S, Hite, Gilbert J, Heyman, Richard A, Gianutsos, Gerald
Format: Article
Language:English
Subjects:
Analgesics, Opioid - chemical synthesis
Analgesics, Opioid - pharmacology
Animals
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - pharmacology
Bridged-Ring Compounds - chemical synthesis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Mice
Organic chemistry
Preparations and properties
Rats
Receptors, Opioid - drug effects
Structure-Activity Relationship
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Summary:The synthesis of a series of 9-phenyl-3,7-diazabicyclanes and 9-(m-hydroxyphenyl)-3,7-diazabicyclanes is described. Members of both series were tested for antinociception in rat tail withdrawal and mouse acetic acid writhing assays. Their affinities for opiate receptors in rat brain homogenate were also determined. The 9-phenyl compounds, 1a-c, were inactive. However, the 9-(m-hydroxyphenyl) analogues, 2a-c, were found to possess significant activity in the writhing assay, comparable to that of morphine. All activity was reversed by naloxone.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00160a054