Synthesis of Aristoquinoline Enantiomers and Their Evaluation at the alpha 3 beta 4 Nicotinic Acetylcholine Receptor
ORGANIC LETTERS(2021)
摘要
The first synthesis of aristoquinoline (1), a naturally occurring nicotinic acetylcholine receptor (nAChR) antagonist, was accomplished using two different approaches. Comparison of the synthetic material's spectroscopic data to that of the isolated alkaloid identified a previously misassigned stereogenic center. An evaluation of each enantiomer's activity at the alpha 3 beta 4 nAChR revealed that (+)-1 is significantly more potent than (-)-1. This unexpected finding suggests that naturally occurring 1 possesses the opposite absolute configuration from indole-containing Aristotelia alkaloids.
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关键词
aristoquinoline enantiomers,α3β4 nicotinic acetylcholine receptor,synthesis
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