1-Oxo-5-hydroxytryptamine:  A Surprisingly Potent Agonist of the 5-HT3 (Serotonin) Receptor

A novel synthetic route to 1-oxo-5-hydroxytryptamine, the benzofuran analogue of serotonin, has been developed. The new synthesis proceeds via the [3+2] cycloaddition of p-benzoquinone and 2,3-dihydrofuran, followed by a Lewis acid-catalyzed isomerization. This molecule proves to be a competent agon...

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Bibliographic Details
Published in:Organic letters 2007-08, Vol.9 (17), p.3205-3207
Main Authors: Kedrowski, Sean M. A, Bower, Kiowa S, Dougherty, Dennis A
Format: Article
Language:English
Subjects:
Benzofurans - chemical synthesis
Benzofurans - pharmacology
Humans
Receptors, Serotonin - drug effects
Serotonin - analogs & derivatives
Serotonin - chemical synthesis
Serotonin - pharmacology
Serotonin Receptor Agonists - chemical synthesis
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Summary:A novel synthetic route to 1-oxo-5-hydroxytryptamine, the benzofuran analogue of serotonin, has been developed. The new synthesis proceeds via the [3+2] cycloaddition of p-benzoquinone and 2,3-dihydrofuran, followed by a Lewis acid-catalyzed isomerization. This molecule proves to be a competent agonist (equipotent to serotonin) of the 5-HT3 receptor, demonstrating that the indolic proton of serotonin is not essential to its activation of the receptor.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol071083s