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

Carla E. Brown; James McNulty; Claudia Bordón; Robert Yolken; Lorraine Jones-Brando

doi:10.1039/c6ob01083k

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

Carla E. Brown, James McNulty, Claudia Bordón, Robert Yolken, Lorraine Jones-Brando

School of Medicine

Research output: Contribution to journal › Article › peer-review

Abstract

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 μM) against in vitro Toxoplasma gondii coupled with little or no cytotoxicity (TD₅₀ ≥ 320 μM) towards the host cells.

Original language	English (US)
Pages (from-to)	5951-5955
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	25
DOIs	https://doi.org/10.1039/c6ob01083k
State	Published - 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity. / Brown, Carla E.; McNulty, James; Bordón, Claudia; Yolken, Robert ; Jones-Brando, Lorraine.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 25, 2016, p. 5951-5955.

Research output: Contribution to journal › Article › peer-review

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

abstract = "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 μM) against in vitro Toxoplasma gondii coupled with little or no cytotoxicity (TD50 ≥ 320 μM) towards the host cells.",

author = "Brown, {Carla E.} and James McNulty and Claudia Bord{\'o}n and Robert Yolken and Lorraine Jones-Brando",

note = "Funding Information: We thank NSERC (JMcN) and the Stanley Medical Research Institute (CB, RY, LJB, JMcN) for financial support of this work. CEB is the recipient of an NSERC postgraduate fellowship. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

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doi = "10.1039/c6ob01083k",

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AU - Brown, Carla E.

AU - McNulty, James

AU - Bordón, Claudia

AU - Yolken, Robert

AU - Jones-Brando, Lorraine

N1 - Funding Information: We thank NSERC (JMcN) and the Stanley Medical Research Institute (CB, RY, LJB, JMcN) for financial support of this work. CEB is the recipient of an NSERC postgraduate fellowship. Publisher Copyright: © The Royal Society of Chemistry 2016. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016

Y1 - 2016

N2 - 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 μM) against in vitro Toxoplasma gondii coupled with little or no cytotoxicity (TD50 ≥ 320 μM) towards the host cells.

AB - 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 μM) against in vitro Toxoplasma gondii coupled with little or no cytotoxicity (TD50 ≥ 320 μM) towards the host cells.

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

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