5196-28-1

Basic information

• Product Name: 5,8-dioxo-5,8-dihydronaphthalen-1-yl acetate
• Synonyms: 1,4-naphthalenedione, 5-(acetyloxy)-; 5,8-Dioxo-5,8-dihydro-1-naphthalenyl acetate; Acetic acid, 5,8-dihydro-5,8-dioxo-1-naphthyl ester
• CAS NO: 5196-28-1
• Molecular Formula: C₁₂H₈O₄
• Molecular Weight: 216.1895
• Mol File: 5196-28-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 403.6°C at 760 mmHg
• Flash Point: 183.5°C
• Density: 1.349g/cm³
• Vapor Pressure: 1E-06mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 5,8-dioxo-5,8-dihydronaphthalen-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-dioxo-5,8-dihydronaphthalen-1-yl acetate(5196-28-1)
• EPA Substance Registry System: 5,8-dioxo-5,8-dihydronaphthalen-1-yl acetate(5196-28-1)

Safety Data

• Hazardous Substances Data: 5196-28-1(Hazardous Substances Data)

Upstream product

• 605-89-0 1,5-diacetoxynaphthalene 
• 83-56-7 1,5-dihydroxynaphthalene 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 91963-30-3 5,8-dimethoxynaphthalen-1-ol 
• 108-24-7 acetic anhydride 
• 94807-85-9 5-hydroxynaphthalen-1-yl acetate 
• 99618-32-3 5,8-Dimethoxy-1-naphthyl ethanoate 

Downstream Products

• 77189-69-6 5-acetoxy-2-bromo-1,4-naphthoquinone 
• 113251-01-7 8-acetoxy-2-(5-dimethylhydrazonofur-2-yl)-1,4-naphthoquinone 
• 68749-86-0 3-Benzyljuglonacetat 
• 1192354-82-7 5-acetoxy-2-phenyl-1,4-naphthoquinone 
• 1192354-81-6 8-acetoxy-2-phenyl-1,4-naphthoquinone 
• 857994-43-5 1,4,5-triacetoxy-2-p-tolylsulfanyl-naphthalene 
• 116595-17-6 5-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione 
• 105245-45-2 (4aR,9aS)-5-Methoxy-4,9,10-trioxo-9a-phenylsulfanyl-1,9,9a,10-tetrahydro-4H-anthracene-4a-carbonitrile 
• 105245-44-1 8-Methoxy-1,4-dioxo-3-phenylsulfanyl-1,4-dihydro-naphthalene-2-carbonitrile 
• 14554-09-7 5,8-dihydroxy-2-methyl-[1,4]naphthoquinone 
• 43101-75-3 9,10-dihydro-8-hydroxy-9,10-dioxoanthracen-1-yl acetate 
• 52869-26-8 5-Acetoxy-1-hydroxy-anthrachinon 
• 129-43-1 1-hydroxyanthraquinone 
• 117554-11-7 1-methoxy-5-nitro-9,10-anthraquinone 

Relevant articles and documents

Synthesis of 4,8-dimethoxy-1-naphthol via an acetyl migration

Based on acetyl migration, an efficient synthesis of 4,8-dimethoxy-1-naphthol (1) has been achieved with high overall yield. Compared with the reported method, there were several advantages. First, the reaction conditions were mild. Second, the workup of each step was much simpler. Third, juglone as the starting material in the synthesis was readily available. The solvent and reaction temperature greatly influenced the migration process.

Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors

SARS-CoV-2 as a positive-sense single-stranded RNA coronavirus caused the global outbreak of COVID-19. The main protease (Mpro) of the virus as the major enzyme processing viral polyproteins contributed to the replication and transcription of SARS-CoV-2 in host cells, and has been characterized as an attractive target in drug discovery. Herein, a set of 1,4-naphthoquinones with juglone skeleton were prepared and evaluated for the inhibitory efficacy against SARS-CoV-2 Mpro. More than half of the tested naphthoquinones could effectively inhibit the target enzyme with an inhibition rate of more than 90% at the concentration of 10 μM. In the structure-activity relationships (SARs) analysis, the characteristics of substituents and their position on juglone core scaffold were recognized as key ingredients for enzyme inhibitory activity. The most active compound, 2-acetyl-8-methoxy-1,4-naphthoquinone (15), which exhibited much higher potency in enzyme inhibitions than shikonin as the positive control, displayed an IC50 value of 72.07 ± 4.84 nM towards Mpro-mediated hydrolysis of the fluorescently labeled peptide. It fit well into the active site cavity of the enzyme by forming hydrogen bonds with adjacent amino acid residues in molecular docking studies. The results from in vitro antiviral activity evaluation demonstrated that the most potent Mpro inhibitor could significantly suppress the replication of SARS-CoV-2 in Vero E6 cells within the low micromolar concentrations, with its EC50 value of about 4.55 μM. It was non-toxic towards the host Vero E6 cells under tested concentrations. The present research work implied that juglone skeleton could be a primary template for the development of potent Mpro inhibitors.

Anti-novel coronavirus naphthoquinone compound and medical application thereof

The invention discloses an anti-novel coronavirus naphthoquinone compound and a medical application of the naphthoquinone compound. The structure of the compound is shown as a formula (I), wherein R1is hydrogen, methyl, ethyl, acetyl or propionyl; and R2 is hydrogen, methyl or ethyl. The compound disclosed by the invention has very strong activity of resisting the novel coronavirus, and can be used for inhibiting 3CL hydrolase (3C-like proteinase, 3CLpro) of the 2019-nCoV novel coronavirus. The in-vitro activity determination experiments show that the enzyme inhibition rate of part of the compounds reaches 99% under the concentration of 1 [mu] M. The naphthoquinone compound disclosed by the invention is clear in structure, simple and convenient in preparation method and high in yield, andhas important significance for developing efficient and low-toxicity novel anti-novel coronavirus drugs.