ChemInform Abstract: EFFECT OF HYDROXY‐1,4‐NAPHTHOQUINONE DERIVATIVES ON PROSTAGLANDIN SYNTHESIS. 2. STUDIES ON 1,4‐NAPHTHOQUINONES

Wurm, G.; Baumann, J.

doi:10.1002/chin.198207160

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“…The organic layer and extracts were combined, dried over Na 2 SO 4. , and evaporated to give the residue, which was chromatographed on SiO 2 (8 g, hexane: EtOAc = 30:1−20:1) to afford the title compound. 2-Ethyl-5-hydroxynaphthalene-1,4-dione (9c; Purity: 98%), 47 5-hydroxy-2-propylnaphthalene-1,4-dione (9d; Purity: >98%), 43 5-hydroxy-2-isobutylnaphthalene-1,4-dione (9e; Purity: 96%), 43 and 2-ethyl-8-hydroxynaphthalene-1,4-dione (9g; Purity: >98%) 48 are the known compounds, and the 1 H NMR data were in good agreement with the literature values. 2-(Cycloheptylmethyl)-5-hydroxynaphthalene-1,4-dione (9b).…”

Section: -Methoxynaphthalen-1-yl Cyclopentanecarboxylate (5amentioning

confidence: 99%

Targeting Pancreatic Cancer with Novel Plumbagin Derivatives: Design, Synthesis, Molecular Mechanism, In Vitro and In Vivo Evaluation

et al. 2023

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Pancreatic tumors grow in an "austerity" tumor microenvironment characterized by nutrient deprivation and hypoxia. This leads to the activation of adaptive pathways in pancreatic cancer cells, promoting tolerance to nutrition starvation and aggressive malignancy. Conventional anticancer drugs are often ineffective against tumors that grow in such austerity condition. Plumbagin, a plant-derived naphthoquinone, has shown potent preferential cytotoxicity against pancreatic cancer cells under nutrient-deprived conditions. Therefore, we synthesized a series of plumbagin derivatives and found that 2-(cyclohexylmethyl)-plumbagin (3f) was the most promising compound with a PC 50 value of 0.11 μM. Mechanistically, 3f was found to inhibit the PI3K/Akt/mTOR signaling pathways, leading to cancer cell death under nutrient-deprived conditions. In vivo studies using pancreatic cancer xenograft mouse models confirmed the efficacy of 3f, demonstrating significant inhibition of tumor growth in a dose-dependent manner. Compound 3f represents a highly promising lead for anticancer drug development based on an antiausterity strategy.

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Section: -Methoxynaphthalen-1-yl Cyclopentanecarboxylate (5amentioning

confidence: 99%

Targeting Pancreatic Cancer with Novel Plumbagin Derivatives: Design, Synthesis, Molecular Mechanism, In Vitro and In Vivo Evaluation

et al. 2023

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ChemInform Abstract: EFFECT OF HYDROXY‐1,4‐NAPHTHOQUINONE DERIVATIVES ON PROSTAGLANDIN SYNTHESIS. 2. STUDIES ON 1,4‐NAPHTHOQUINONES

Abstract: Auf den im Formelschema angegebenen Wegen werden die Naphthochinone (IV), (V), (IX), (X) und (XI) hergestellt.

Cited by 1 publication

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Targeting Pancreatic Cancer with Novel Plumbagin Derivatives: Design, Synthesis, Molecular Mechanism, In Vitro and In Vivo Evaluation

Targeting Pancreatic Cancer with Novel Plumbagin Derivatives: Design, Synthesis, Molecular Mechanism, In Vitro and In Vivo Evaluation

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