Carbon Monoxide-Releasing Activity of Plant Flavonoids DOI Creative Commons
Lucie Muchová,

Mária Šranková,

Sriram Balasubramani

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 31, 2024

Flavonoids are naturally occurring compounds found in fruits, vegetables, and other plant-based foods, they known for their health benefits, such as UV protection, antioxidant, anti-inflammatory, antiproliferative properties. This study investigates whether flavonoids, quercetin 2,3-dehydrosilybin, can act photoactivatable carbon monoxide (CO)-releasing molecules under physiological conditions. CO has been recently recognized an important signaling molecule. Here, we show that upon direct irradiation, was released from both flavonoids PBS with chemical yields of up to 0.23 equiv, which increased almost unity by sensitized photooxygenation involving singlet oxygen. Photoreleased reduced cellular toxicity caused high flavonol concentrations, partially restored mitochondrial respiration, superoxide production induced rotenone levels, influenced the G0/G1 G2/M phases cell cycle, showing effects. The findings highlight potential 2,3-dehydrosilybin CO-photoreleasing chemopreventive therapeutic implications human pathology suggest possible roles plant biology.

Language: Английский

Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton DOI

Dong-Sheng Ji,

Xin Zhang,

Peiqin Zhang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 709 - 714

Published: Jan. 7, 2025

Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via ortho-acyl diazo compounds, which are rapidly intercepted by oxygen atom an intermolecular acyl group to form cyclic 1,3-dipole. The in situ generated reactive 1,3-dipole undergoes facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.2.1]-oxo-bridged compounds.

Language: Английский

Citations

2
Emerging progress: photochemical transformation of nitroso compounds DOI

Ze‐Le Chen,

Qiangqiang Li, Armido Studer

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 17, 2024

Language: Английский

Citations

6
Rapid access to 3-substituted bicyclo[1.1.1]pentanes DOI

Katherine I. Burton,

David W. C. MacMillan

Chem, Journal Year: 2025, Volume and Issue: unknown, P. 102537 - 102537

Published: April 1, 2025

Language: Английский

Citations

0
Facile Access to Hindered Ethers via Photoinduced O–H Bond Insertions DOI Creative Commons
Yu Zhang, Xinyu Han,

Dong Li

et al.

ACS Central Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Language: Английский

Citations

0
Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones DOI
Pokhriyal Yamini, Akanksha Babbar, Dongari Yadagiri

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6035 - 6040

Published: July 10, 2024

Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report light-driven intramolecular cyclopropanation alkene-tethered

Language: Английский

Citations

2
Facile Access to Hindered Ethers via Photoinduced O-H Bond Insertions DOI Creative Commons
Yu Zhang, Xinyu Han,

Dong Li

et al.

Published: July 15, 2024

The synthesis of the hindered and polyfluorinated dialkyl ethers poses challenges owing to bulkiness tertiary alcohols low nucleophilicity alcohols. Additionally, associated competitive side reactions always provide poor reactivities. Although certain strategies, such as electrocatalytic decarboxylation hydroalkoxylation, have been explored, a straightforward method for obtaining with structural diversity remains elusive. In this study, we proposed photoinduced approach that involved in-situ formation singlet carbenes followed by O-H insertions access ethers. This successfully converted diverse congested into their corresponding challenging Moreover, other nucleophiles phenols, H2O, thiols, silanols, tributyltin hydride etc. were tolerable obtain valuable products. gram-scale marketed drugs modification complex molecules demonstrated practicality approach. detailed mechanistic studies elucidated key intermediates reaction mechanisms.

Language: Английский

Citations

1
Access to Isoxazoles via Photo-oxygenation of Furan Tethered α-Azidoketones DOI

Uma Devi Newar,

Sylvia Jaya Kumar,

Anupriya Borah

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12378 - 12386

Published: Aug. 22, 2024

Photocatalyst-free visible light-enabled direct oxygenation of furan-tethered α-azidoketones was studied. The reaction yielded various products depending on the substituents, with isoxazoles forming as major products. findings suggest that singlet oxygen generated during and reacted in a [4 + 2] fashion to yield endoperoxides, which rearranged multiple ways generate isoxazoles. Some synthesized were evaluated α-glucosidase inhibitors, three them 5bi, 5bj, 5bl exhibited good activity IC50 values 454.57 ± 29.34, 147.84 2.28, 272.58 42.06 μM, respectively, when compared standard drug acarbose (IC50 = 1224.33 126.72 μM).

Language: Английский

Citations

1
Organocatalytic Deoxygenative [3+2] Cycloaddition of N-Hydroxyamides with Alkynes to Access Isoxazoles DOI
Haixiang Wang, Yan Sun,

Wentong Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

Although the transition-metal-catalyzed [3+2] cycloadditions to access isoxazoles have been described well, organocatalytic methods remain underdeveloped. Herein, we report use of an organophosphine catalyst for preparation a series with exceptional regioselectivity via cycloaddition

Language: Английский

Citations

0
Carbon Monoxide-Releasing Activity of Plant Flavonoids DOI Creative Commons
Lucie Muchová,

Mária Šranková,

Sriram Balasubramani

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 31, 2024

Flavonoids are naturally occurring compounds found in fruits, vegetables, and other plant-based foods, they known for their health benefits, such as UV protection, antioxidant, anti-inflammatory, antiproliferative properties. This study investigates whether flavonoids, quercetin 2,3-dehydrosilybin, can act photoactivatable carbon monoxide (CO)-releasing molecules under physiological conditions. CO has been recently recognized an important signaling molecule. Here, we show that upon direct irradiation, was released from both flavonoids PBS with chemical yields of up to 0.23 equiv, which increased almost unity by sensitized photooxygenation involving singlet oxygen. Photoreleased reduced cellular toxicity caused high flavonol concentrations, partially restored mitochondrial respiration, superoxide production induced rotenone levels, influenced the G0/G1 G2/M phases cell cycle, showing effects. The findings highlight potential 2,3-dehydrosilybin CO-photoreleasing chemopreventive therapeutic implications human pathology suggest possible roles plant biology.

Language: Английский

Citations

0