Synthesis of Benzodioxinopyrroles as selective α 2-adrenoceptor antagonists

A novel series of tetrahydrobenzodioxinopyrroles has been identified as potent and selective α 2-adrenoceptor antagonists. Convergent syntheses have been developed that allowed the preparation of analogues and their enantiomers. A compound of particular interest is the 5-fluoro substituted analogue...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1995-12, Vol.3 (12), p.1595-1603
Main Authors: Kitchin, J., Borthwick, A.D., Brodie, A.C., Cherry, P.C., Crame, A.J., Pipe, A.J., Procopiou, P.A., Seaman, M.A., Turnbull, J.P.
Format: Article
Language:English
Subjects:
Adrenergic alpha-2 Receptor Antagonists
Adrenergic alpha-Antagonists - chemical synthesis
Adrenergic alpha-Antagonists - chemistry
Adrenergic alpha-Antagonists - pharmacology
Animals
In Vitro Techniques
Male
Mice
Molecular Structure
Piperoxan - analogs & derivatives
Piperoxan - chemical synthesis
Piperoxan - chemistry
Piperoxan - pharmacology
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - pharmacology
Rats
Stereoisomerism
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Summary:A novel series of tetrahydrobenzodioxinopyrroles has been identified as potent and selective α 2-adrenoceptor antagonists. Convergent syntheses have been developed that allowed the preparation of analogues and their enantiomers. A compound of particular interest is the 5-fluoro substituted analogue (fluparoxan). Tetrahydro-1 H-benzodioxino[2,3- c]pyrroles (1) have been synthesized and found to be potent and selective α 2-adrenoceptor antagonists. A compound of particular interest is Fluparoxan (1; R 1 = H, R 2 = F).
ISSN:0968-0896
1464-3391
DOI:10.1016/0968-0896(95)00143-3