Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

Macedo, Maíra Bidart de; Kimmel, Roman; Urankar, Damijana; Gazvoda, Martin; Peixoto, António; Cools, Freya; Torfs, Eveline; Verschaeve, Luc; Lima, Émerson Silva; Lyčka, Antonı́n; Milićević, David; Klásek, Antonı́n; Cos, Paul; Kafka, Stanislav; Košmrlj, Janez; Cappoen, Davie

doi:10.1016/j.ejmech.2017.06.061

Cited by 25 publications

(11 citation statements)

References 38 publications

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“…Alongside the many derivatives of the parent coumarin scaffold, there is the nitrogen-containing structural analogue known as carbostyril (Figure ). − Though not as widely utilized as coumarin, carbostyril is the subject of many structure–property relationship studies, and it shows promise for use in both pharmaceutical discovery and fluorescence imaging applications. , These carbostyril analogues expand on the applications of the coumarin family through modifying the lactone core to a lactam. With further alteration of this core, new applications, functionality, and fluorescent properties are expected from this widely used fluorophore.…”

Section: Introductionmentioning

confidence: 99%

Amplification of the Quantum Yields of 2-λ⁵-Phosphaquinolin-2-ones through Phosphorus Center Modification

et al. 2019

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We report the synthesis and characterization of P-phenyl modified phosphorus-and nitrogen-containing phosphaquinolinone heterocycles. The change from −OPh to −Ph results in a marked increase in the quantum yield of the scaffold as well as a moderate red-shifting of the emission. While calculations suggest that π to π* transitions are dominant, intramolecular charge transfer (ICT) also contributes in the excited state. Solution-and solid-state studies of the dimerization of this new congener to the P-phenoxy variant are also reported, showing retention of the dimerization behavior in this scaffold. Article pubs.acs.org/joc

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Section: Introductionmentioning

confidence: 99%

Amplification of the Quantum Yields of 2-λ⁵-Phosphaquinolin-2-ones through Phosphorus Center Modification

et al. 2019

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“…All reagents, including 2-ethynylaniline, were purched from Energy Chemistry Co. Ltd., and used without further purification. CO2 and Ar were purchased from Hangzhou Jinggong Special Gas Co. Ltd. 1 H NMR and 13 C NMR studies were carried out with a Bruker AVANCE III 500 (500 MHz, 125 MHz) spectrometer or Bruker AVANCE III HD 600 (600 MHz, 150 MHz) with CDCl3, D2O or DMSO-d6 as the solvent.…”

Section: Methodsmentioning

confidence: 99%

Silver-Catalyzed Conversion of CO2 and 2-Ethynylanilines into 4-Hydroxyquinolin-2(1H)-ones in Protic Ionic Liquid at Atmospheric Pressure

Qi¹,

Yuan²,

Zhu³

et al. 2022

HETEROCYCLES

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Hydroxyquinolin-2(1H)-ones are core structural subunits frequently found in many pharmacological compounds and the synthesis of this kind of compounds is highly desirable. An efficient protic ionic liquid and AgNO3 catalytic system was developed for the preparation of various 4-hydroquinolin-2(1H)-ones from CO2 and 2-ethynylanilines in moderate to excellent yields (65-94%). It was found that [HTMG][Im], a simple and easily prepared protic ionic liquid comprising a 1,1,3,3-tetramethylguanidinium cation and a imidazolide anion, could act as both the solvent and reaction promoter, and that the reaction could be efficient carried out with a mount of 2 mol% AgNO3 under atmospheric pressure of CO2 at 60 ℃. This method provides a new approach for the synthesis of 4hydroxyquinolin-2(1H)-ones.Due to the environmental advantage of CO2 as a C1 building block, as well as the importance of CO2 emission reduction in mitigate climate change, chemical conversion of CO2 has paid much attention in recent decades. In this field, ionic liquids (IL), because of their unique properties, have showed outstanding performance in CO2 capture and utilization processes. Many value-added chemicals have been synthesized from CO2, using ILs as solvents and/or catalysts, such as quinazoline-2,4-(1H,3H)-diones, 1-6 cyclic carbonates, 7 2-benzimidazolones, 8 carbamates, 9 oxazolidinones, 10 ureas, 11 and so on. Although much progress has been made, expanding the scope of the chemical conversion of CO2 in ILs, especially under mild conditions is still a challenge. 4-Hydroxyquinolin-2(1H)-one derivatives are important intermediates due to their pharmacological activities, 12 including antitubercular potency, 13 anti-HIV activity, 14 antibacterial activity, 15 and anticancer 1486

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“…3Y-MMP [66]. This compound was previously isolated as a plant metabolite from Isatis tinctoria (Brassicaceae) and displayed anti-tuberculosis activity with an IC 90 of 6.8 µM [66][67][68]. An extensive isolation report in 2020 described the isolation of six new HAQs, including the highly unusual sulfide and benzyl derivatives H3a and H7b, in addition to fifteen known AQs, three AQNOs, and the tetrhydroquinoline T7 [24].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

2020

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The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the Pseudomonas and Burkholderia genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from Pseudomonas aeruginosa. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in Pseudomonas aeruginosa. Many of the best-studied examples contain simple hydrocarbon side-chains, but more recent studies have revealed a wide range of structurally diverse examples from multiple bacterial genera, including those with aromatic, isoprenoid, or sulfur-containing side-chains. In addition to their well-known antimicrobial properties, alkylquinolones have been reported with antimalarial, antifungal, antialgal, and antioxidant properties. Here we review the structural diversity and biological activity of these intriguing metabolites.

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Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

Cited by 25 publications

References 38 publications

Amplification of the Quantum Yields of 2-λ⁵-Phosphaquinolin-2-ones through Phosphorus Center Modification

Amplification of the Quantum Yields of 2-λ⁵-Phosphaquinolin-2-ones through Phosphorus Center Modification

Silver-Catalyzed Conversion of CO2 and 2-Ethynylanilines into 4-Hydroxyquinolin-2(1H)-ones in Protic Ionic Liquid at Atmospheric Pressure

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

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Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

Cited by 25 publications

References 38 publications

Amplification of the Quantum Yields of 2-λ5-Phosphaquinolin-2-ones through Phosphorus Center Modification

Amplification of the Quantum Yields of 2-λ5-Phosphaquinolin-2-ones through Phosphorus Center Modification

Silver-Catalyzed Conversion of CO2 and 2-Ethynylanilines into 4-Hydroxyquinolin-2(1H)-ones in Protic Ionic Liquid at Atmospheric Pressure

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

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Amplification of the Quantum Yields of 2-λ⁵-Phosphaquinolin-2-ones through Phosphorus Center Modification

Amplification of the Quantum Yields of 2-λ⁵-Phosphaquinolin-2-ones through Phosphorus Center Modification