Visible light-induced deoxygenation/cyclization of salicylic acid derivatives and aryl acetylene for the synthesis of flavonoids

He, Chaoyin; Ji, Mengmeng; Sun, Xinhui; Luo, Hui; Li, Chao; Tong, Huixin; Zhang, Weiya; Sun, Zhe; Chu, W. K.

doi:10.1039/d2cc01538b

Cited by 6 publications

(4 citation statements)

References 29 publications

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“…The second step is the Baker–Venkataraman rearrangement reaction of O-acetylphenol p-toluate in the presence of potassium hydroxide to produce the corresponding propanedione. Finally, propanedione was cyclized under the co-catalysis of glacial acetic acid and concentrated sulfuric acid to produce the final target product 4′-methyflavanone [ 46 , 47 ]. Fortunately, the final product was obtained in good yield.…”

Section: Methodsmentioning

confidence: 99%

AIEE-Active Flavones as a Promising Tool for the Real-Time Tracking of Uptake and Distribution in Live Zebrafish

Luo

et al. 2023

IJMS

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In recent years, aggregation-induced emission enhancement (AIEE) molecules have shown great potential for applications in the fields of bio-detection, imaging, optoelectronic devices, and chemical sensing. Based on our previous studies, we investigated the fluorescence properties of six flavonoids and confirmed that compounds 1–3 have good aggregation-induced emission enhancement (AIEE) properties through a series of spectroscopic experiments. Compounds with AIEE properties have addressed the limitation imposed by the aggregation-caused quenching (ACQ) of classic organic dyes owing to their strong fluorescence emission and high quantum yield. Based on their excellent fluorescence properties, we evaluated their performance in the cell and we found that they could label mitochondria specifically by comparing their Pearson correlation coefficients (R) with Mito Tracker Red and Lyso-Tracker Red. This suggests their future application in mitochondrial imaging. Furthermore, studies of uptake and distribution characterization in 48 hpf zebrafish larvae revealed their potential for monitoring real-time drug behavior. The uptake of compounds by larvae varies significantly across different time cycles (between uptake and utilization in the tissue). This observation has important implications for the development of visualization techniques for pharmacokinetic processes and can enable real-time feedback. More interestingly, according to the data presented, tested compounds aggregated in the liver and intestine of 168 hpf larvae. This finding suggests that they could potentially be used for monitoring and diagnosing liver and intestinal diseases.

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Section: Methodsmentioning

confidence: 99%

AIEE-Active Flavones as a Promising Tool for the Real-Time Tracking of Uptake and Distribution in Live Zebrafish

Luo

et al. 2023

IJMS

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“…[ 82 ] However, aberrant tryptophan metabolism and dysbiosis of gut microbiota may lead to changes in AhR activity during aging that might contribute to the acceleration of the aging processes. [ 83 ] Similar to the “imbalance” in the gut microbial community, dysbiosis of the microbiota in the gut, “dysbiosis” of the skin microbiota is equally important by affecting skin homeostasis, exacerbating a variety of skin diseases, and affecting disease diagnosis and treatment. For example, Staphylococcus aureus (SA) was found on the skin of patients with atopic dermatitis (AD) at the site of lesions caused by AD that can impede the function of the skin barrier or activate the inflammatory response.…”

Section: Ahr and Hallmarks Of Agingmentioning

confidence: 99%

Aryl hydrocarbon receptor: Linking environment to aging process in elderly patients with asthma

Yang,

Wan,

et al. 2024

Chinese Medical Journal

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Aging is a significant risk factor for various diseases, including asthma, and it often leads to poorer clinical outcomes, particularly in elderly individuals. It is recognized that age-related diseases are due to a time-dependent accumulation of cellular damage, resulting in a progressive decline in cellular and physiological functions and an increased susceptibility to chronic diseases. The effects of aging affect not only the elderly but also those of younger ages, posing significant challenges to global healthcare. Thus, understanding the molecular mechanisms associated with aging in different diseases is essential. One intriguing factor is the aryl hydrocarbon receptor (AhR), which serves as a cytoplasmic receptor and ligand-activated transcription factor and has been linked to the aging process. Here, we review the literature on several major hallmarks of aging, including mitochondrial dysfunction, cellular senescence, autophagy, mitophagy, epigenetic alterations, and microbiome disturbances. Moreover, we provide an overview of the impact of AhR on these hallmarks by mediating responses to environmental exposures, particularly in relation to the immune system. Furthermore, we explore how aging hallmarks affect clinical characteristics, inflammatory features, exacerbations, and the treatment of asthma. It is suggested that AhR signaling may potentially play a role in regulating asthma phenotypes in elderly populations as part of the aging process.

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“…The photomediated formation of acyl radicals directly from acids mostly employs DMDC or phosphines (e.g., PPh 3 , PMe 2 Ph) as additives and [Ir(III)] as photocatalyst. In 2022, Chu and co-workers [ 32 ] developed a protocol to form acyl radicals directly from acids utilizing Ph 2 S as activator and the organic dye Mes–Acr–MeClO 4 as photocatalyst ( Scheme 5 ). They demonstrated intermolecular radical cyclization of o -hydroxybenzoic acid derivatives with terminal alkynes to afford flavone derivatives.…”

Section: Reviewmentioning

confidence: 99%

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

Roy,

Sardar,

Mallick

et al. 2024

Beilstein J. Org. Chem.

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Alkyl and acyl radicals play a critical role in the advancement of chemical synthesis. The generation of acyl and alkyl radicals by activation of C–O bonds using visible-light photoredox catalysis offers a mild and environmentally benign approach to useful chemical transformations. Alcohols, carboxylic acids, anhydrides, xanthates, oxalates, N-phthalimides, and thiocarbonates are some examples of alkyl and acyl precursors that can produce reactive radicals by homolysis of the C–O bond. These radicals can then go through a variety of transformations that are beneficial for the construction of synthetic materials that are otherwise difficult to access. This study summarizes current developments in the use of organic photocatalysts, transition-metal photoredox catalysts, and metallaphotocatalysts to produce acyl and alkyl radicals driven by visible light.

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Visible light-induced deoxygenation/cyclization of salicylic acid derivatives and aryl acetylene for the synthesis of flavonoids

Abstract: A visible light-induced photocatalytic strategy for synthesis of flavonoids was developed through deoxygenative/cyclization reaction of salicylic acid derivatives with aryl acetylene by diphenyl sulfide as an O-transfer reagent. Based on...

Cited by 6 publications

References 29 publications

AIEE-Active Flavones as a Promising Tool for the Real-Time Tracking of Uptake and Distribution in Live Zebrafish

AIEE-Active Flavones as a Promising Tool for the Real-Time Tracking of Uptake and Distribution in Live Zebrafish

Aryl hydrocarbon receptor: Linking environment to aging process in elderly patients with asthma

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

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