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Issue 3, 2018
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Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

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Abstract

In this study, the (S)-enantiomers of the aporphine alkaloids, nuciferine and roemerine, were prepared via a synthetic route involving catalytic asymmetric hydrogenation and both stereoisomers were evaluated in vitro for functional activity at human 5-HT2 and adrenergic α1 receptor subtypes using a transforming growth factor-α shedding assay. Both enantiomers of each of the compounds were found to act as antagonists at 5-HT2 and α1 receptors. (R)-roemerine was the most potent compound at 5-HT2A and 5-HT2C receptors (pKb = 7.8–7.9) with good selectivity compared to (S)-roemerine at these two receptors and compared to its activity at 5-HT2B, α1A, α1B and α1D receptors.

Graphical abstract: Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

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Submitted
15 Dec 2017
Accepted
09 Feb 2018
First published
26 Feb 2018

Med. Chem. Commun., 2018,9, 576-582
Article type
Research Article

Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

H. L. Heng, C. F. Chee, S. P. Chin, Y. Ouyang, H. Wang, M. J. C. Buckle, D. R. Herr, I. C. Paterson, S. W. Doughty, N. Abd. Rahman and L. Y. Chung, Med. Chem. Commun., 2018, 9, 576 DOI: 10.1039/C7MD00629B

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