Work

Synthesis of Aristoquinoline Enantiomers and Their Evaluation at the α3β4 Nicotinic Acetylcholine Receptor

Year: 2021

Type: article

Abstract: 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 α3β4 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.1c02057

Authors: Malaika D. Argade, Carolyn J. Straub, Lisa E. Rusali, Bernard D. Santarsiero, Andrew P. Riley

Institution: University of Illinois Chicago

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Center for Clinical and Translational Science, University of Illinois at Chicago, National Institutes of Health, National Center for Advancing Translational Sciences, National Center for Complementary and Integrative Health

Awards: Institutional Career Development, G5071817090, Research Training in Natural Product Complementary and Integrative Health