Synthesis and structure-activity relationships for new 6-fluoroquinoline derivatives with antiplasmodial activity

Hochegger, Patrick; Faist, Johanna; Seebacher, Werner; Saf, Robert; Mäser, Pascal; Kaiser, Marcel; Weis, Robert

doi:10.1016/j.bmc.2019.03.061

Cited by 15 publications

(12 citation statements)

References 25 publications

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“…NMR spectra were performed on Bruker DRX-300 AVANCE spectrometer at the "Cité Innovation" Sidi Mohamed Ben Abellah University of Fez . 1 H NMR spectra were recorded at 300 MHz, and 13 C NMR spectra were recorded at 75 MHz. Samples were dissolved in DMSO-d6 or/in CDCl3.…”

Section: General Methodsmentioning

confidence: 99%

“…The five amino acids (alanine, serine, phenylglycine, phenylalanine and tryptophan) were converted towards their methylated esters groups, The synthesized compounds purified on liquid chromatography column using silica gel as a stationary phase and were obtained with good yields ranging from 60 to 80%. Their chemical structures were elucidated by both techniques 1 H and 13 C NMR and mass-spectrometry.…”

Section: Synthesis Of Quinoline-carboxamidesmentioning

confidence: 99%

“…The structural modification induced a change with improving the activity and conferring some efficiency treatment against pneumologic infections 5 . Some quinoline derivatives have been also synthesized and know by their antibacterial activities 6 , potent intestinal antiseptic 7 , agent anticancer 8 , analgesic 9 , antiallergic 10 , used for the treatment of Alzheimer's disease (AD) 11 , antitinephritic 12 , antiplasmodial activity 13 , antimalarial 14 , antihypertensive 15 , anti-HIV 16 and present an antitumoral activities 17 .…”

Section: Introductionmentioning

confidence: 99%

“…In this work, we report the synthesis of ten new quinoline-4-carboxamides compounds. Their structural characterizations by both Nuclear Magnetic Resonance 1 H and 13 C and mass-spectrometry, as well as, the evaluation of their antibacterial activities against 9 types of bacteria.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

et al. 2019

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Ten new quinoline-carboxamides have been synthesized using the coupling reaction between 2-oxo-1,2-dihydroquinoline-4-carboxylic acid as a substrate and five different amino ester at room temperature with basic media (triethylamine). The products were obtained with a good yield ranging from 60 to 80 % and were structurally characterized by 1H and 13C NMR spectroscopy and mass spectrometry. The antibacterial activities of the synthesized compounds have been evaluated against 9 strains of bacteria and compared to references (erythromycin, ofloxacin, ticarcillin, oxacillin, ampicillin, norfloxacin, ceftazidim, cefotaxim). The results showed that the majority of carboxamides-quinoline ester groups present a larger inhibition diameters than those of the antibiotics references. The highest antibacterial activity in vitro against the Enterococcus feacalis has been revealed for compound 1a (methyl 2-oxo-1.2-dihydroquinoline-4-yl-L-alaninate).

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Section: General Methodsmentioning

confidence: 99%

Section: Synthesis Of Quinoline-carboxamidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

et al. 2019

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“…[6] Some 2-aryl-6-fluoroquinoline-4-carboxamides have recently been found to have high antiplasmodial activity against Plasmodium berghei. [7] Trifluoromethyl-substituted quinolines are mostly prepared from CF 3 -substituted building blocks by adaptation of classical strategies. Scheme 1 shows several approaches of this kind leading to 4-CF 3 -quinolines.…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of 4‐CF₃‐Quinolines from 1‐Trifluoromethyl‐prop‐2‐yne 1‐Iminium Salts and Arylamines

et al. 2021

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A convenient synthesis of 4-trifluoromethyl-quinolines from 1trifluoromethyl-prop-2-yne 1-iminium triflates and anilines in a one-pot two-step Michael addition/intramolecular cyclization sequence is reported. With ring-substituted anilines, a wide range of 4-CF 3 -quinolines bearing additional substituents and functional groups in the C-2, C-6, and C-8 positions were prepared, mostly in high yields. Even a 4-CF 3 -5-Me-quinoline could be obtained. From mono-Boc protected 1,4-and 1,3-phenylenediamine, 2-aryl-substituted 6-amino-4-CF 3 -quinoline and 7-amino-4-CF 3 -quinoline, respectively, were prepared. 4-CF 3 -benzo[h]quinolines were obtained from the mentioned acetylenic iminium salts and 1-naphthylamine. With N-monosubstituted aromatic amines such as N-methylaniline and 1,2,3,4-tetrahydroquinoline, N-substituted 4-CF 3 -quinolinium salts and pyrrolo[1,2-a:3,4-c']diquinoline derivatives bearing two CF 3 substituents could be prepared.

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Benzyne‐Induced Ring Opening Reactions of DABCO: Synthesis of 1,4‐Disubstituted Piperazines and Piperidines

Seo

Kim

2020

Adv Synth Catal

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The 2‐(4‐phenylpiperazin‐1‐yl)ethan‐1‐amine scaffold is a structurally important motif that occurs frequently in medicinal and pharmaceutical chemistry. Despite the significance of this moiety, general strategies for its synthesis to date have required multistep methods and have been very limited, such as the use of SNAr‐type reactions. Herein, we describe a synthetic methodology employing benzynes, 1,4‐diazabicyclo(2.2.2)octane (DABCO), and nitrogen nucleophiles to access these privileged organic compounds. The established protocol proved to be a transition‐metal‐free, mild reaction that proceeded via a quaternary ammonium salt formed from the benzyne and DABCO.magnified image

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Synthesis and structure-activity relationships for new 6-fluoroquinoline derivatives with antiplasmodial activity

Cited by 15 publications

References 25 publications

Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

A Convenient Synthesis of 4‐CF₃‐Quinolines from 1‐Trifluoromethyl‐prop‐2‐yne 1‐Iminium Salts and Arylamines

Benzyne‐Induced Ring Opening Reactions of DABCO: Synthesis of 1,4‐Disubstituted Piperazines and Piperidines

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Synthesis and structure-activity relationships for new 6-fluoroquinoline derivatives with antiplasmodial activity

Cited by 15 publications

References 25 publications

Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

A Convenient Synthesis of 4‐CF3‐Quinolines from 1‐Trifluoromethyl‐prop‐2‐yne 1‐Iminium Salts and Arylamines

Benzyne‐Induced Ring Opening Reactions of DABCO: Synthesis of 1,4‐Disubstituted Piperazines and Piperidines

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A Convenient Synthesis of 4‐CF₃‐Quinolines from 1‐Trifluoromethyl‐prop‐2‐yne 1‐Iminium Salts and Arylamines