Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity

Authors: Coelho L, Cristiano MLS, Fausto R, Henriques MS, Horta P, Kuş N, Nogueira F, O'Neill PM, Paixão JA
Publication Year: 2015
Journal: Journal of Organic Chemistry
Link: https://pubs.acs.org/doi/10.1021/acs.joc.5b02169%20

Recent publications report in vitro activity of quinolone 3-esters against the bc1 protein complex of Plasmodium falciparum and the parasite. Docking studies performed in silico at the yeast Qo site established a key role for the 4-oxo and N-H groups in drug-target interactions. Thus, the possibility of 4-oxoquinoline/4-hydroxyquinoline tautomerism may impact in pharmacologic profiles and […]
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On the ordeal of quinolone preparation via cyclisation of aryl-enamines; Synthesis and structure of ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylate

Authors: Brás EM, Cristiano MLS, Fausto R, Henriques MSC, Horta P, Murtinheira F, Nogueira F, O'Neill PM, Paixão JA
Publication Year: 2017
Journal: Pure and Applied Chemistry
Link: https://www.degruyter.com/view/j/pac.2017.89.issue-6/pac-2016-1119/pac-2016-1119.xml

Recent studies directed to the design of compounds targeting the bc1 protein complex of Plasmodium falciparum, the parasite responsible for most lethal cases of malaria, identified quinolones (4-oxo-quinolines) with low nanomolar inhibitory activity against both the enzyme and infected erythrocytes. The 4-oxo-quinoline 3-ester chemotype emerged as a possible source of potent bc1 inhibitors, prompting us to expand the library of available […]
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Novel endoperoxide-based transmission-blocking antimalarials with liver- and blood-schizontocidal activities

Authors: Albuquerque IS, Amewu R, Capela R, Gut J, Lopes F, Marti F, Meireles P, Miranda D, Moreira R, Mota MM, Nogueira F, O'Neill PM, Oliveira R, Paiva I, Prudencio M, Rosenthal PJ
Publication Year: 2013
Journal: ACS Medicinal Chemistry Letters
Link: http://www.ncbi.nlm.nih.gov/pubmed/24900781

In a search for effective compounds against both the blood- and liver-stages of infection by malaria parasites with the ability to block the transmission of the disease to mosquito vectors, a series of hybrid compounds combining either a 1,2,4-trioxane or 1,2,4,5-tetraoxane and 8-aminoquinoline moieties were synthesized and screened for their antimalarial activity.
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Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity

On the ordeal of quinolone preparation via cyclisation of aryl-enamines; Synthesis and structure of ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylate

Novel endoperoxide-based transmission-blocking antimalarials with liver- and blood-schizontocidal activities

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