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 H Yolken; Lorraine V 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 H Yolken, Lorraine V Brando

School of Medicine

Research output: Contribution to journal › Article

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

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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Brown, C. E., McNulty, J., Bordón, C., Yolken, R. H., & Brando, L. V. (2016). Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity. Organic and Biomolecular Chemistry, 14(25), 5951-5955. https://doi.org/10.1039/c6ob01083k

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