Design, synthesis and biological evaluation of substituted flavones and aurones as potential anti-influenza agents

Chintakrindi, Anand S.; Gohil, Devanshi; Chowdhary, Abhay; Kanyalkar, Meena

doi:10.1016/j.bmc.2019.115191

Cited by 24 publications

(11 citation statements)

References 18 publications

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“…Although less active than flavone counterparts, compound 108 provided a very potent profile by combining an exquisite anti-IAV activity (EC 50 = 35 nM) with a good therapeutic index value of ∼5000. 157 An additional study tried to retrieve IAV neuraminidase inhibitors from a docking-based virtual screening. The approach was overall successful, as several aurone analogues presented IC 50 values below 50 nM in the series.…”

Section: Neurochemical Activities Inhibition Of Monoamine Oxidases (M...mentioning

confidence: 99%

“…Surprisingly, while initially developed for targeting IAV neuraminidase, the compounds exhibited only moderate action against the enzyme (IC 50 = 37–45 μM) but managed to induce significant viral reduction at concentrations 1000 times lower (EC 50 = 30–50 nM). Although less active than flavone counterparts, compound 108 provided a very potent profile by combining an exquisite anti-IAV activity (EC 50 = 35 nM) with a good therapeutic index value of ∼5000 . An additional study tried to retrieve IAV neuraminidase inhibitors from a docking-based virtual screening.…”

Section: Biological Activities Of Hemiindigoidsmentioning

confidence: 99%

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Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

et al. 2022

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Hemiindigoids comprise a range of natural and synthetic scaffolds that share the same aromatic hydrocarbon backbone as well as promising biological and optical properties. The encouraging therapeutic potential of these scaffolds has been unraveled by many studies over the past years and uncovered representants with inspiring pharmacophoric features such as the acetylcholinesterase inhibitor donezepil and the tubulin polymerization inhibitor indanocine. In this review, we summarize the last advances in the medicinal potential of hemiindigoids, with a special attention to molecular design, structure–activity relationship, ligand-target interactions, and mechanistic explanations covering their effects. As their strong fluorogenic potential and photoswitch behavior recently started to be highlighted and explored in biology, giving rise to the development of novel fluorescent probes and photopharmacological agents, we also discuss these properties in a medicinal chemistry perspective.

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Section: Neurochemical Activities Inhibition Of Monoamine Oxidases (M...mentioning

confidence: 99%

Section: Biological Activities Of Hemiindigoidsmentioning

confidence: 99%

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

et al. 2022

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“…Importantly, aurone is one of the privileged structures in medicinal chemistry and is commonly associated with various pharmacologically active compounds. [47][48][49] Aurones have been demonstrated as phytoalexins, which are used by plants in their defense mechanism against numerous infections. Perhaps due to their scarcity in nature, aurones have received less attention than other avonoids and not been broadly studied for their biological activities.…”

Section: Introductionmentioning

confidence: 99%

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

et al. 2021

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“…Thus, compound 1 n is identified as a potent inhibitor of monoamine oxidases (MAO) − the enzymes involved in pathophysiological mechanisms of many psychiatric and neurological disorders [48] . Compound 1 h is recently found to show pronounced effect against influenza A virus (IAV) [49] . Derivatives 1 h , 1 l , 1 n , 1 q demonstrate antibacterial activity against several gram‐positive organisms ( Bacillus subtilis , Staphylococcus epidermidis , Staphylococcus aureus ) [50] .…”

Section: Resultsmentioning

confidence: 99%

Design of Aurone‐Based Dual‐State Emissive (DSE) Fluorophores

Berdnikova

Bolte

Suta

2023

Chemistry A European J

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The development of dual-state emissive (DSE) fluorophores, i. e. organic molecules showing balanced emission in both solution and as molecular solids, has recently become an emerging approach in material science, biology, sensing, and optoelectronics. However, the majority of existing DSE fluorophores represents structural modifications of the scaffolds known for their aggregation-induced emission (AIE) properties, e. g., tetraphenylethylenes (TFE), triphenylamines (TFA), and others. In this study, we introduce aurones as an easily accessible scaffold for the construction of DSE fluorophores and describe the main design principles allowing to achieve the balanced emission in both solution and solid state. Herein, we present the solid-state fluorescence in a systematic series of aurone derivatives for the first time. We propose that the newly found DSE properties of aurones in combination with their established biological activity can be applied efficiently in biomedical studies and diagnostic tools.

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Design, synthesis and biological evaluation of substituted flavones and aurones as potential anti-influenza agents

Cited by 24 publications

References 18 publications

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

Design of Aurone‐Based Dual‐State Emissive (DSE) Fluorophores

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