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Synthesis 2023; 55(14): 2241-2252
DOI: 10.1055/s-0042-1752658
DOI: 10.1055/s-0042-1752658
paper
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry
Synthesis of Clausena Alkaloids Using Unique Ring Expansion of Dihydroisoquinolines and Their Cholinesterase Inhibitory Activity
Funding: Thailand Science Research and Innovation (TSRI, Grant Number FRB660044/0240), Chulabhorn Royal Academy (Project Code 180874) and Chulabhorn Research Institute (Grant Numbers 36824/4274394 and 36827/4274407).
Abstract
A facile and direct synthetic entry to the carbon skeleton of Clausena alkaloids, the benzo[d]azocin-4-one, is reported featuring the ring expansion of 1-phenyldihydroisoquinoline derivatives initially triggered by oxazolone under environmentally benign conditions in a one-pot procedure. Functionalization of the eight-membered lactam framework provided a set of Clausena alkaloid derivatives. Some derivatives show a promising inhibition toward acetylcholinesterase and a better selectivity index than the previously used Alzheimer’s disease (AD) drug, tacrine, and the currently used AD drug, galantamine.
Key words
Clausena alkaloids - ζ-clausenamides - balasubramides - benzo[d]azocinones - eight-membered lactams - ring expansionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1752658.
- Supporting Information
Publication History
Received: 31 January 2023
Accepted after revision: 24 February 2023
Article published online:
12 April 2023
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