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Green and Fast Synthesis of 2-Arylidene-indan-1,3-diones Using a Task-Specific Ionic Liquid.

ABSTRACT: A novel method for condensation reaction of indan-1,3-dione with various aldehydes which are efficiently catalyzed by a task-specific ionic liquid, 2-hydroxyethylammonium formate, to provide the corresponding 2-arylidenindane-1,3-diones has been developed. This green, low-cost, high-yield, and fast reaction takes place at room temperature without the use of any solvent and catalyst. A plausible reaction mechanism that involves ionic liquid-assisted activation is also discussed. This work is the first report of ionic liquids as a reaction medium and catalyst for the synthesis of 2-arylidenindane-1,3-diones.

SUBMITTER: Alizadeh A

PROVIDER: S-EPMC7658926 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Green and Fast Synthesis of 2-Arylidene-indan-1,3-diones Using a Task-Specific Ionic Liquid.

Alizadeh Abdolhamid A Beiranvand Zahra Z Safaei Zahra Z Khodaei Mohammad M MM Repo Eveliina E

ACS omega 20201028 44

A novel method for condensation reaction of indan-1,3-dione with various aldehydes which are efficiently catalyzed by a task-specific ionic liquid, 2-hydroxyethylammonium formate, to provide the corresponding 2-arylidenindane-1,3-diones has been developed. This green, low-cost, high-yield, and fast reaction takes place at room temperature without the use of any solvent and catalyst. A plausible reaction mechanism that involves ionic liquid-assisted activation is also discussed. This work is the ...[more]

PMID: 33195915

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Project description:A series of specific task ionic liquids (ILs) based on a pyridiniumhydrazone scaffold in combination with hexafluorophosphate (PF?-), tetrafluoroboron (BF?-) and/or trifluoroacetate (CF?COO-) counter anion, were designed and characterized by IR, NMR and mass spectrometry. The reactions were conducted under both conventional and green ultrasound procedures. The antifungal potential of the synthesized compounds 2-25 was investigated against 40 strains of Candida (four standard and 36 clinical isolates). Minimum inhibitory concentrations (MIC90) of the synthesized compounds were in the range of 62.5-2000 ?g/mL for both standard and oral Candida isolates. MIC90 results showed that the synthesized 1-(2-(4-chlorophenyl)-2-oxoethyl)-4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-pyridin-1-ium hexafluorophosphate (11) was found to be most effective, followed by 4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-1-(2-(4-nitrophenyl)-2-oxoethyl)-pyridin-1-ium hexafluorophosphate (14) and 1-(2-ethoxy-2-oxoethyl)-4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)pyridin-1-ium hexafluorophosphate (8). All the Candida isolates showed marked sensitivity towards the synthesized compounds. Ergosterol content was drastically reduced by more active synthesized compounds, and agreed well with MIC90 values. Confocal scanning laser microscopy (CLSM) results showed that the red colored fluorescent dye enters the test agent treated cells, which confirms cell wall and cell membrane damage. The microscopy results obtained suggested membrane-located targets for the action of these synthesized compounds. It appears that the test compounds might be interacting with ergosterol in the fungal cell membranes, decreasing the membrane ergosterol content and ultimately leading to membrane disruption as visible in confocal results. The present study indicates that these synthesized compounds show significant antifungal activity against Candida which forms the basis to carry out further in vivo experiments before their clinical use.

Dataset Information

Green and Fast Synthesis of 2-Arylidene-indan-1,3-diones Using a Task-Specific Ionic Liquid.

Publications

Green and Fast Synthesis of 2-Arylidene-indan-1,3-diones Using a Task-Specific Ionic Liquid.

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