4923-55-1

Basic information

• Product Name: 2-hydroxyjuglone
• Synonyms: 2-hydroxyjuglone;2,5-Dihydroxy-1,4-naphthalenedione;2,5-Dihydroxy-1,4-naphthoquinone;2,5-Dihydroxynaphthalene-1,4-dione;2-HJ
• CAS NO: 4923-55-1
• Molecular Formula: C₁₀H₆O₄
• Molecular Weight: 190.153
• Mol File: 4923-55-1.mol

Chemical Properties

• Boiling Point: 430°Cat760mmHg
• Flash Point: 228°C
• Appearance: /
• Density: 1.639g/cm³
• Vapor Pressure: 3.71E-08mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-hydroxyjuglone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxyjuglone(4923-55-1)
• EPA Substance Registry System: 2-hydroxyjuglone(4923-55-1)

Safety Data

• Hazardous Substances Data: 4923-55-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxyjuglone is used as a potential anti-cancer agent for its ability to inhibit cancer cell growth and proliferation. It is particularly effective against various types of cancer, including solid malignancies, due to its ability to interfere with essential cellular processes and signaling pathways in cancer cells.
Used in Chemical Synthesis:
2-Hydroxyjuglone is used as a reagent in the preparation of substituted 1,4-naphthoquinones, which are valuable compounds in the pharmaceutical and chemical industries. These substituted naphthoquinones have a wide range of applications, including their use as anti-cancer agents, due to their unique chemical structures and biological activities.

InChI:InChI=1/C10H6O4/c11-6-3-1-2-5-9(6)7(12)4-8(13)10(5)14/h1-4,11-12H

Upstream product

• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 15254-76-9 8-hydroxy-2-methoxynaphthalene-1,4-dione 
• 83-56-7 1,5-dihydroxynaphthalene 
• 4923-57-3 2-chlorojuglone 
• 15127-94-3 2-methoxy-5-hydroxy-1,4-naphthoquinone 
• 15255-29-5 2,3-epoxy-5-hydroxy-2,3-dihydro-1,4-naphthoquinone 
• 49598-85-8 scytalone 
• 24291-20-1 1,2,4,5-tetracetoxynaphthalene 
• 605-89-0 1,5-diacetoxynaphthalene 
• 60549-39-5 5-acetoxy-2-chloronaphthalene-1,4-dione 
• 33892-75-0 5-Methoxy-1-tetralone 
• 106697-18-1 2-Brom-5-hydroxy-3-methoxy-1,4-naphthochinon 
• 18855-91-9 3-Bromo-2-methoxyjuglone 
• 106697-16-9 3-chloro-5-hydroxy-2-methoxy-1,4-naphthoquinone 

Downstream Products

• 88497-92-1 diodantunezone 
• 123297-90-5 (–)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione 
• 1021299-35-3 (S)-NQ₈₀₁ MTPA ester 
• 62042-67-5 2,5-Dihydroxy-3-methyl-[1,4]naphthochinon 
• 123297-90-5 5-hydroxy-2-(1-hydroxyethyl)naphtho<2.3-b>furan-4,9-dione 
• 13378-90-0 6-Acetyl-2-hydroxy-juglon 
• 137039-30-6 5-hydroxy-2-phenyl-1,4-naphthoquinone 

Relevant articles and documents

OXYDATION DU NAPHTALENEDIOL-1,5 PAR LE SUPEROXYDE DE POTASSIUM EN PHASE HETEROGENE

The oxydation of 1,5-dihydroxynaphthalene by potassium superoxide is essentially an interfacial solid/liquid reaction, which leads to 2,5- and 3,5-dihydroxy-1,4-naphthoquinones.The reaction proceeds in two steps through the formation of 5-hydroxy-1,4-naphthoquinone.The mechanism of the reaction is discussed.

Asymmetric synthesis of natural cis-dihydroarenediols using tetrahydroxynaphthalene reductase and its biosynthetic implications

Asymmetric reduction of hydroxynaphthoquinones to secondary metabolites, (3S,4R)-3,4,8- A nd (2S,4R)-2,4,8-trihydroxy-1-tetralone, a putative biosynthetic diketo intermediate and a probable natural analogue, (3S,4R)-7-acetyl-3,4,8-trihydroxy-6-methyl-3,4-

Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones

A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure–activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.

Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity

To establish the structure-activity relationship of 5-hydroxy-1,4-naphthoquinones toward anticancer activity, a series of its derivatives were prepared and tested for the activity (IC50 in μM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among them 2 (IC50: 2.3; 2.0; 1.4 μM), 6 (IC50: 1.9; 2.2; 1.3 μM), 9 (IC50: 0.7; 1.7; 0.9 μM) and 10 (IC50:1.7; 1.0; 1.2 μM) showed moderate to excellent activity. Our perception toward the DNA substitution of alkoxy groups at the C2 position of these naphthoquinones for the anticancer activity led us to investigate their reactivity of substitution toward dimethylamine as a nucleophile. The ease of the substitution of alkoxy groups at the C2 position with dimethylamine is strongly accelerated by hydroxyl group at C5 position and is well correlated with the found anticancer activity results.

Synthesis and cytotoxic activity of a small naphthoquinone library: First synthesis of juglonbutin

A synthetic protocol has been designed to synthesize grecoketidone (2k), 5-hydroxylapachol (2g), and the recently discovered natural products juglonbutin (2o) and its derivatives, leading to a small library of different 1,4-naphthoquinones with the intention of finding new active compounds. Within our collection, 2-O-alkylated naphthoquinones with an ester functionality in the side-chain and a free OH group at C-5 showed the best activities. Compounds 2f, 2m, and 2n showed GI50 values against 12 tumor cell lines in the lower micromolar range and juglonbutin (2o) showed remarkably efficient inhibition of the glycogen synthase kinase 3β with an IC50 value of 2.03 μM. Furthermore, studies on the mode of action of the most active cytotoxic compounds have been carried out. To the best of our knowledge, this is the first report on the synthesis of juglonbutin (2o) and its biological activity. Copyright

Activated zeolites and heteropolyacids: An efficient catalysts for the synthesis of triacetoxyaromatic precursors of hydroxyquinones

The Thiele-Winter reaction is of interest for synthesis of triacetoxyaromatic precursors of hydroquinones. Liquid acid such as, chlorosulfonic acid and solid acids like heteropolyacids have an efficient catalyst can effectively replace sulfuric acid in acetoxylation reaction of quinones without use of organic solvent at room temperature.

Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity.

Synthesis and evaluation of bioactive naphthoquinones from the Brazilian medicinal plant, Tabebuia avellanedae

A series of naphthoquinones based on the naphtho[2,3-b]furan-4,9-dione skeleton such as (-)-5-hydroxy-2-(1′-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione (1) and its positional isomer, (-)-8-hydroxy-2-(1′-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione (2), which are secondary metabolites found in the inner bark of Tabebuia avellanedae, were stereoselectively synthesized and their biological activities were evaluated in conjunction with those of their corresponding enantiomers. Compound 1 exhibited potent antiproliferative effect against several human tumor cell lines, but its effect against some human normal cell lines was much lower than that of mitomycin. On the other hand, its enantiomer (R)-1 was less active toward the above tumor cell lines than 1. The antiproliferative effect of 2 against all tumor cell lines was significantly reduced. These results indicated the presence of the phenolic hydroxy group at C-5 is of great important for increasing antiproliferative effect. In addition, 1 also showed higher cancer chemopreventive activity than 2, while there were no significant differences between 1 and 2 in antimicrobial activity. Both compounds displayed modest antifungal and antibacterial activity (Gram-positive bacteria), whereas they were inactive against Gram-negative bacteria.

Preparation of optically active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4, 9-diones having anticancer activities

An object of the present invention is to provide a method for efficiently preparing (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]-furan-4,9-dione useful as a medicine at a low cost and in large amounts. According to the present invention, the desired (S)

Stereoselective synthesis and cytotoxicity of a cancer chemopreventive naphthoquinone from Tabebuia avellanedae

Stereoselective synthesis of 1, one of biologically active naphthoquinones from a Brazilian traditional medicine Tabebuia avellanedae, was achieved by utilizing Noyori reduction as a key step. Compound 1 displayed potent cytotoxicity against several human tumor cell lines, whereas it showed lower cytotoxicity against some human normal cell lines compared with that of mitomycin. On the other hand, its enantiomer was less active toward the tumor cell lines than 1.