Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity. Issue 25 (3rd June 2016)

• Record Type: Journal Article
• Authors: Brown, Carla E.; McNulty, James; Bordón, Claudia; Yolken, Robert; Jones-Brando, Lorraine
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 25(2016)
• Page Start: 5951
• Page End: 5955
• Publication Date: 2016-06-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01083k
• Languages: English
• ISSNs: 1477-0520

Abstract

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. 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.