Green Synthetic Approaches to Furoylnaphthohydroquinone and Juglone

Benites, Julio; Michael, Cortes; Luis, Miranda; Estela, Cynthia; Ríos, David; Jorge, Arenas; A., Valderrama Jaime

doi:10.4067/s0717-97072014000200012

Cited by 3 publications

(2 citation statements)

References 10 publications

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“…The preparation of the phenylaminojuglone derivatives was achieved via a two synthetic step sequence from 1,5-dihydroxynaphthalene 1 and the selected phenylamines 3 according to 1 and Figure 1 . In the first step, sensitized photooxygenation of compound 1 on water gave 5-hydroxy-1,4-naphthoquinone (2, juglone) in 64% yield [ 46 ]. Further reaction of juglone 2 with the phenylamines in ethanol [ 47 , 48 ] at room temperature provided the respective phenylaminojuglones 4–15.…”

Section: Resultsmentioning

confidence: 99%

In VitroInhibition ofHelicobacter pyloriGrowth by Redox Cycling Phenylaminojuglones

Benites

Toledo

Salas

et al. 2018

Oxidative Medicine and Cellular Longevity

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Infection by Helicobacter pylori increases 10 times the risk of developing gastric cancer. Juglone, a natural occurring 1,4-naphthoquinone, prevents H. pylori growth by interfering with some of its critical metabolic pathways. Here, we report the design, synthesis, and in vitro evaluation of a series of juglone derivatives, namely, 2/3-phenylaminojuglones, as potential H. pylori growth inhibitors. Results show that 5 out of 12 phenylaminojuglones (at 1.5 μg/mL) were 1.5–2.2-fold more active than juglone. Interestingly, most of the phenylaminojuglones (10 out of 12) were 1.1–2.8 fold more active than metronidazole, a known H. pylori growth inhibitor. The most active compound, namely, 2-((3,4,5-trimethoxyphenyl)amino)-5-hydroxynaphthalene-1,4-dione 7, showed significant higher halo of growth inhibitions (HGI = 32.25 mm) to that of juglone and metronidazole (HGI = 14.50 and 11.67 mm). Structural activity relationships of the series suggest that the nature and location of the nitrogen substituents in the juglone scaffold, likely due in part to their redox potential, may influence the antibacterial activity of the series.

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Section: Resultsmentioning

confidence: 99%

In VitroInhibition ofHelicobacter pyloriGrowth by Redox Cycling Phenylaminojuglones

Benites

Toledo

Salas

et al. 2018

Oxidative Medicine and Cellular Longevity

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“…Demethylation of ethyl ( E )-3-(5,8-dimethoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acrylate was achieved through a boron tribromide adduct, which was hydrolyzed by the addition of water to afford product 20 (41% yield from 12 ). The photooxidation method 31 was used to prepare 5-hydroxynaphthalene-1,4-dione (juglone) 11 from 1,5-dihydroxynaphthalene by bubbling molecular oxygen in methanol in the presence of Rose Bengal catalyst and green light-emitting diode (LED).…”

Section: Resultsmentioning

confidence: 99%

Identification of New Mono/Dihydroxynaphthoquinone as Lead Agents That Inhibit the Growth of Refractive and Triple-Negative Breast Cancer Cell Lines

et al. 2019

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Human epidermal growth factor receptor 2 (HER2) is overexpressed in nearly 20–30% of breast cancers and is associated with metastasis resulting in poor patient survival and high recurrence. The dual EGFR/HER2 kinase inhibitor lapatinib has shown promising clinical results, but its limitations have also led to the resistance and activation of tumor survival pathways. Following our previous investigation of quinones as HER2 kinase inhibitors, we synthesized several naphthoquinone derivatives that significantly inhibited breast tumor cells expressing HER2 and trastuzumab-resistant HER2 oncogenic isoform, HER2Δ16. Two of these compounds were shown to be more effective than lapatinib at the inhibition of HER2 autophosphorylation of Y1248. Compounds 7 (5,8-dihydroxy-2-methylnaphthalene-1,4-dione) and 9 (2-(bromomethyl)-5,8-dihydroxynaphthalene-1,4-dione) inhibited HER2-expressing MCF-7 cells (IC 50 0.29 and 1.76 μM, respectively) and HER2Δ16-expressing MCF-7 cells (IC 50 0.51 and 1.76 μM, respectively). Compound 7 was also shown to promote cell death in multiple refractory breast cancer cell lines with IC 50 values ranging from 0.12 to 2.92 μM. These compounds can function as lead compounds for the design of a new series of nonquinonoid structural compounds that can maintain a similar inhibition profile.

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Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor

et al. 2020

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A series of photochemical transformations has been successfully conducted under continuous-flow conditions in a concentrating solar trough reactor. Photoacylations and [2+2]-photocycloadditions involving 1,4-naphthoquinones gave the corresponding photoproducts in moderate to high yields with residence times of 70min. Likewise, acetone-sensitized photodecarboxylations involving phthalimides furnished the corresponding benzylated hydroxy phthalimidines in good to excellent yields and purity with residence times of 40min. Compared with corresponding exposures to direct sunlight conducted in a solar float, flow operation generally gave superior conversions and subsequent yields.

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Green Synthetic Approaches to Furoylnaphthohydroquinone and Juglone

Cited by 3 publications

References 10 publications

In VitroInhibition ofHelicobacter pyloriGrowth by Redox Cycling Phenylaminojuglones

In VitroInhibition ofHelicobacter pyloriGrowth by Redox Cycling Phenylaminojuglones

Identification of New Mono/Dihydroxynaphthoquinone as Lead Agents That Inhibit the Growth of Refractive and Triple-Negative Breast Cancer Cell Lines

Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor

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