Convenient One-Pot Synthesis of Chromone Derivatives and Their Antifungal and Antibacterial Evaluation

Ghani, Sherif B. Abdel; Mugisha, Patrick J.; Wilcox, Juliet C.; Gado, E. A. M.; Medu, Erere O.; Lamb, Andrew J.; Brown, Richard C. D.

doi:10.1080/00397911.2011.647222

Cited by 31 publications

(10 citation statements)

References 22 publications

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“…We previously described the synthesis of HHQ and PQS derivatives with nitrogen in position 1 exchanged by oxygen and sulfur [33]. In our efforts to optimize the synthesis of these heteroatom derivatives we used a one-pot reaction for the synthesis of 2-heptyl-chromen-4-one (1-O-HHQ, 4 ) which includes esterification, Baker–Venkataraman rearrangement and subsequent acid-catalyzed ring closure to affort the 1-O-HHQ in 60% yield [36] (Scheme 1). …”

Section: Resultsmentioning

confidence: 99%

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

Prothiwa¹,

Szamosvári²,

Glasmacher³

et al. 2016

Beilstein J. Org. Chem.

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The human pathogen Pseudomonas aeruginosa uses the pqs quorum sensing system to coordinate the production of its broad spectrum of virulence factors to facilitate colonization and infection of its host. Hereby, the enzyme PqsD is a virulence related quorum sensing signal synthase that catalyzes the central step in the biosynthesis of the Pseudomonas quinolone signals HHQ and PQS. We developed a library of cysteine reactive chemical probes with an alkyne handle for fluorescence tagging and report the selective and highly sensitive in vitro labelling of the active site cysteine of this important enzyme. Interestingly, only one type of probe, with a reactive α-chloroacetamide was capable of covalently reacting with the active site. We demonstrated the potential of our probes in a competitive labelling platform where we screened a library of synthetic HHQ and PQS analogues with heteroatom replacements and found several inhibitors of probe binding that may represent promising scaffolds for the development of customized PqsD inhibitors as well as a chemical toolbox to investigate the activity and active site specificity of the enzyme.

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Section: Resultsmentioning

confidence: 99%

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

Prothiwa¹,

Szamosvári²,

Glasmacher³

et al. 2016

Beilstein J. Org. Chem.

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“…Chromones substituted with halogens at C6‐position gave the corresponding products in 45–60 % yield (compounds 2 k–m ). Remarkably, 6‐bromo‐2‐cyclohexylchromone ( 2 m ) has been found to possess extremely potent antifungal properties with an inhibitor concentration (IC 50 ) value of 7 ng cm −2 11d. 6‐Methylchromone gave the cross‐coupling product 2 p in good yield of 76 %.…”

Section: Methodsmentioning

confidence: 99%

Hypervalent Iodine‐Mediated Selective Oxidative Functionalization of (Thio)chromones with Alkanes

Narayan

Antonchick

2014

Chemistry A European J

101

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C-C bond formation is the most fundamental way for the chain propagation in organic molecules. This achievement through tandem oxidation of two different C-H bonds represents the state of the art in organic synthesis. Selective functionalization of the ubiquitous aliphatic C-H bonds offers an attractive option for this oxidative cross-coupling methodology. To develop such a methodology under mild and "metal-free" conditions remains challenging. Herein, we report hypervalent iodine-mediated selective oxidative functionalization of aliphatic C-H bonds of alkanes with chromones and (thio)chromones. A wide range of alkanes, both cyclic and acyclic, has been found to react selectively and predictably in good yields. The developed methodology is also the first report of a direct oxidative functionalization of the C-2 position of (thio)chromones with alkanes to access bioactive compounds.

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“…As early as the late 19th century, Khellin was extracted from the fruit of the Umbellifera, which was widely distributed in eastern Mediterranean countries, and was used as the first chromone drug in clinical applications [ 5 ]. Meanwhile, biological activity results showed that both natural and synthetic chromone compounds had a wide range of biological activities, such as antifungal [ 6 , 7 ], antibacterial [ 6 ], anticancer [ 8 ], and antiviral [ 9 ] activity. Thiochromanone, a kind of chromone compound, is an important substance in the synthesis of various active molecules that are extensively used in the intermediate skeleton of drugs and has attracted more and more attention due to their extensive biological activities, including antiviral [ 10 ], antibacterial [ 11 , 12 ], antifungal [ 11 , 13 , 14 , 15 ], herbicidal [ 16 , 17 ], and insecticidal [ 18 ] activity.…”

Section: Introductionmentioning

confidence: 99%

Novel Thiochromanone Derivatives Containing a Sulfonyl Hydrazone Moiety: Design, Synthesis, and Bioactivity Evaluation

Chi

Xiao

et al. 2021

Molecules

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A series of novel thiochromanone derivatives containing a sulfonyl hydrazone moiety were designed and synthesized. Their structures were determined by 1H-NMR, 13C-NMR, and HRMS. Bioassay results showed that most of the target compounds revealed moderate to good antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri. Compound 4i had the best inhibitory activity against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri, with the EC50 values of 8.67, 12.65, and 10.62 μg/mL, which were superior to those of Bismerthiazol and Thiodiazole-copper. Meanwhile, bioassay results showed that all of the target compounds proved to have lower antifungal activities against Sclerotinia sclerotiorum, Fusarium oxysporum, Gibberella zeae, Rhizoctonia solani, Verticillium dahlia, and Botrytis cinerea than those of Carbendazim.

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Convenient One-Pot Synthesis of Chromone Derivatives and Their Antifungal and Antibacterial Evaluation

Cited by 31 publications

References 22 publications

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

Hypervalent Iodine‐Mediated Selective Oxidative Functionalization of (Thio)chromones with Alkanes

Novel Thiochromanone Derivatives Containing a Sulfonyl Hydrazone Moiety: Design, Synthesis, and Bioactivity Evaluation

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