123297-90-5

Basic information

• Product Name: 5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
• Synonyms: 5-Hydroxy-2-(1-hydroxyethyl)naphtho(2,3-b)furan-4,9-dione; naphtho[2,3-b]furan-4,9-dione, 5-hydroxy-2-(1-hydroxyethyl)-
• CAS NO: 123297-90-5
• Molecular Formula: C₁₄H₁₀O₅
• Molecular Weight: 258.2262
• Mol File: 123297-90-5.mol

Chemical Properties

• Boiling Point: 465°C at 760 mmHg
• Flash Point: 235°C
• Density: 1.506g/cm³
• Vapor Pressure: 1.91E-09mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: 5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione(123297-90-5)
• EPA Substance Registry System: 5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione(123297-90-5)

Safety Data

• Hazardous Substances Data: 123297-90-5(Hazardous Substances Data)

Upstream product

• 4923-55-1 2-Hydroxyjuglon 
• 1369328-74-4 (S)-2-(dimethylamino)-5-hydroxy-3-(3-hydroxybut-1-yn-1-yl)naphthalene-1,4-dione 
• 52431-65-9 3-Bromojuglone 
• 18512-17-9 2-(dimethylamino)-5-hydroxy-1,4-naphthalenedione 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 87549-97-1 2-acetyl-5-hydroxynaphtho<2,3-b>furan-4,9-dione 
• 138995-49-0 Tetradecanoic acid 1-(4,9-dioxo-5-tetradecanoyloxy-4,9-dihydro-naphtho[2,3-b]furan-2-yl)-ethyl ester 
• 1369329-23-6 2-(dimethylamino)-5-hydroxy-3-(3-hydroxybut-1-yn-1-yl)naphthalene-1,4-dione 
• 1369329-28-1 2,5-dihydroxy-3-iodonaphthalene-1,4-dione 
• 2028-63-9 but-3-yn-2-ol 

Downstream Products

• 1021299-35-3 (S)-NQ₈₀₁ MTPA ester 

Relevant articles and documents

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.

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.

Structure-activity relationship studies of antimicrobial naphthoquinones derived from constituents of tabebuia avellanedae

In this study, based on our previous study, derivatives of naphtho[2,3-b]furan-4,9-diones were synthesized and their antimicrobial activities were evaluated. The screening of these naphthoquinones revealed that the fluorine-containing NQ008 compound exhib

Concise synthesis of heterocycle-fused naphthoquinones by employing sonogashira coupling and tandem addition-elimination/intramolecular cyclization

A concise method for the synthesis of heterocycle-fused naphthoquinones such as naphtho[2,3-b]-furan-4,9-dione, 1H-benz[f]indole-4,9-dione, and naphtho[2,3-b]thiophene-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-

NOVEL PREPARATION OF ANTICANCER-ACTIVE TRICYCLIC COMPOUNDS VIA ALKYNE COUPLING REACTION

The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R1 is optionally substituted C1-6 alkyl, etc.; W is O, S or NR2; R2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R1 is the same as defined above, and a compound of formula (III) or (IV): wherein R2 is the same as defined above; R3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

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)

ANTICANCER COMPOUND, INTERMEDIATE THEREFOR, AND PROCESSES FOR PRODUCING THESE

The present invention provides a method for easily and inexpensively preparing a racemate or an optically-active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione in high yields, 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione which is useful as an intermediate for preparing NFD, and an anticancer agent comprising 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione as an active ingredient. Said 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione is obtained in 4 or 5 steps by using comparatively inexpensive 5-hydroxynaphthalene-1,4-dione (also referred to as juglone) as a starting material.

Studies on the Structure and Stereochemistry of Cytotoxic Furanonaphthoquinones from Tabebuia impetiginosa: 5- and 8-Hydroxy-2-(1-hydroxyethyl)naphthofuran-4,9-diones

Chemical investigation of the bark of Tabebuia impetiginosa (Bignoniaceae) afforded cytotoxic furanonaphthoquinones, including 5-hydroxy-2-(1-hydroxyethyl)naphthofuran-4,9-dione and its 8-hydroxy isomer.The position of the phenolic group in these two compounds was established by X-ray crystallography.The furanonaphthoquinones were found to be mixtures of both enantiomers in different proportions, i.e., (for the 5-hydroxy isomer) R:S 1:23 and (for the 8-hydroxy isomer) R:S 3:1.The synthesis of the racemic naphthofurans, their optical resolution into enantiomerically pure forms, and the determination of their absolute stereochemistry are described.The structure of kigelinone was also established to be that of the 5-hydroxy isomer, not the 8-hydroxy one, through this study.