77189-69-6

Basic information

• Product Name: 5-Acetoxy-2-bromo-1,4-naphthoquinone
• Synonyms: 2-Bromo-5-acetoxy-1,4-naphthoquinone;2-Bromo-5-acetoxynaphthalene-1,4-dione;5-Acetoxy-2-bromo-1,4-naphthoquinone
• CAS NO: 77189-69-6
• Molecular Formula: C₁₂H₇BrO₄
• Molecular Weight: 295.08558
• Mol File: 77189-69-6.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 5-Acetoxy-2-bromo-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Acetoxy-2-bromo-1,4-naphthoquinone(77189-69-6)
• EPA Substance Registry System: 5-Acetoxy-2-bromo-1,4-naphthoquinone(77189-69-6)

Safety Data

• Hazardous Substances Data: 77189-69-6(Hazardous Substances Data)

Usage

Uses

5-Acetoxy-2-bromo-1,4-naphthoquinone is an intermediate in the synthesis of Plumbagin-d3 (P627002). Plumbagin-d3 is labelled Plumbagin (P627000) which induces apoptosis in cancer cells. It also inhibits NADPH oxidase 4 in a time- and dose-dependent manner.

Upstream product

• 141612-12-6 Acetic acid 6-bromo-5,8-dihydroxy-naphthalen-1-yl ester 
• 94807-85-9 5-hydroxynaphthalen-1-yl acetate 
• 83-56-7 1,5-dihydroxynaphthalene 
• 108-24-7 acetic anhydride 
• 87712-57-0 5-acetoxy-2,4,4-tribromonaphthalen-1-one 
• 605-89-0 1,5-diacetoxynaphthalene 
• 87728-27-6 5-acetoxy-2,4-dibromonaphthol 
• 5196-28-1 juglone acetate 

Downstream Products

• 98-95-3 nitrobenzene 
• 1383471-02-0 acetic acid 3-(4-fluorophenyl)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-5-yl ester 
• 1383471-03-1 3-(4-fluorophenyl)-5-hydroxynaphtho[2,3-d]isoxazole-4,9-dione 
• 1383471-07-5 1-benzyl-4-(5-methoxy-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-3-yl)pyridinium bromide 
• 1383471-08-6 4-(5-acetoxy-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-3-yl)-1-benzylpyridinium bromide 
• 1383471-09-7 1-benzyl-4-(5-hydroxy-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-3-yl)pyridinium bromide 
• 741265-59-8 (2S,3S,6S)-6-((5S,6S)-1,8-Bis-benzyloxy-5-hydroxy-3-hydroxymethyl-7,12-dimethoxy-5,6-dihydro-benzo[a]anthracen-6-yloxy)-2-methyl-tetrahydro-pyran-3-ol 

Relevant articles and documents

Mechanism of Bromination of 1,5-Diacetoxynaphthalene

-

Naphthoquinone derivative or a salt thereof as an active ingredient and horticultural fungicide containing (by machine translation)

[A] a naphthoquinone derivative or salt thereof, or a salt thereof as an active ingredient horticultural fungicide containing said derivative, and use thereof. [Solution] the ingredient, represented by the following formula. [In the formula, R1 And R2 Is, for example, are each independently a hydrogen atom, a halogen, amino, substituted C1 - C6 The alkylcarbonyloxy groups such as shown, however, R1 And R2 Is, not simultaneously hydrogen atoms, R3 Is, for example, C1 - C6 Alkyl, C3 - C8 Cycloalkyl, C1 - C6 Alkoxy groups, R5 R6 N - shown as, R4 Is, a hydrogen atom or a halogen atom, here, R5 And R6 The, each independently hydrogen atom or C1 - C6 The alkyl groups, R5 And R6 The, the nitrogen atom to which they are attached together, may form a hetero ring, however, R5 And R6 The, are not simultaneously hydrogen atoms. ][Drawing] no (by machine translation)

Novel heat shock protein 90 inhibitors suppress P-glycoprotein activity and overcome multidrug resistance in cancer cells

Heat Shock Protein 90 (Hsp90) chaperone interacts with a broad range of client proteins involved in cancerogenesis and cancer progression. However, Hsp90 inhibitors were unsuccessful as anticancer agents due to their high toxicity, lack of selectivity against cancer cells and extrusion by membrane transporters responsible for multidrug resistance (MDR) such as P-glycoprotein (P-gp). Recognizing the potential of new compounds to inhibit P-gp function and/or expression is essential in the search for effective anticancer drugs. Eleven Hsp90 inhibitors containing an isoxazolonaphtoquinone core were synthesized and evaluated in two MDR models comprised of sensitive and corresponding resistant cancer cells with P-gp overexpression (human non-small cell lung carcinoma and colorectal adenocarcinoma). We investigated the effect of Hsp90 inhibitors on cell growth inhibition, P-gp activity and P-gp expression. Structure-activity relationship analysis was performed in respect to cell growth and P-gp inhibition. Compounds 5, 7, and 9 directly interacted with P-gp and inhibited its ATPase activity. Their potential P-gp binding site was identified by molecular docking studies. In addition, these compounds downregulated P-gp expression in MDR colorectal carcinoma cells, showed good relative selectivity towards cancer cells, while compound 5 reversed resistance to doxorubicin and paclitaxel in concentration-dependent manner. Therefore, compounds 5, 7 and 9 could be promising candidates for treating cancers with P-gp overexpression.