里特反应
化学
亚胺
天然产物
腈
烟碱乙酰胆碱受体
烟碱激动剂
乙酰胆碱受体
立体化学
组合化学
有机化学
受体
生物化学
催化作用
作者
Carolyn J. Straub,Lisa E. Rusali,Andrew P. Riley
标识
DOI:10.1021/acsmedchemlett.4c00506
摘要
The alkaloid aristoquinoline (1a) and its non-natural isomer isoaristoquinoline (1b) are inhibitors of the α3β4 nicotinic acetylcholine receptor (nAChR). A Ritter-like reaction was used to form the [3.3.1]- and [3.2.1]-azabicyclic scaffolds found in 1a and 1b, respectively. Although the electronic properties of the aryl nitrile did not influence product ratios or enhance the enantioselectivity of the reaction, changes to the aliphatic core led to the exclusive formation of [3.2.1]-azabicyclic products. Reduction of the imine products yielded a series of 1a and 1b derivatives that inhibit α3β4 nAChRs, including several derivatives with improved potency relative to those of 1a and 1b.
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