Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity

被引：25

作者：

Brown, Carla E. ^{[1
]}

McNulty, James ^{[1
]}

Bordon, Claudia ^{[2
]}

Yolken, Robert ^{[2
]}

Jones-Brando, Lorraine ^{[2
]}

机构：

[1] McMaster Univ, Dept Chem & Chem Biol, Hamilton, ON L8S 4M1, Canada

[2] Johns Hopkins Univ, Sch Med, Dept Pediat, Stanley Div Dev Neurovirol, 600 N Wolfe St, Baltimore, MD 21287 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 25期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ONE-POT SYNTHESIS; SUBSTITUTED QUINOLINES; TOXOPLASMA-GONDII; CUPRIC ACETATE; DERIVATIVES; IMINES; ARYLATION; ALDEHYDES; ALCOHOLS; ANILINE;

D O I：

10.1039/c6ob01083k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the preparation of 2-carboxyl-3-aryl quinoline derivatives from anilines, ethyl glyoxalate and enol ethers as phenylacetaldehyde surrogates is reported. The three-component coupling reaction occurs rapidly under mild conditions in dichloromethane catalysed by TFA. The method allows a more direct access to 3-aryl quinolines, sidestepping issues encountered with phenylacetaldehyde derivatives. This chemistry was used to prepare quinolines with 3-diarylether functionality that showed low micromolar efficacy (IC50 range: 5-26 mu M) against in vitro Toxoplasma gondii coupled with little or no cytotoxicity (TD50 >= 320 mu M) towards the host cells.

引用

页码：5951 / 5955

页数：5

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