5656-82-6

Basic information

• Product Name: naphtho(2,3-b)furan-4,9-dione
• Synonyms: naphtho(2,3-b)furan-4,9-dione;4,9-Dihydronaphtho[2,3-b]furan-4,9-dione;Avicequinone B
• CAS NO: 5656-82-6
• Molecular Formula: C12H6 O3
• Molecular Weight: 198.17
• Mol File: 5656-82-6.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 359°Cat760mmHg
• Flash Point: 169.3°C
• Appearance: /
• Density: 1.396g/cm³
• Vapor Pressure: 2.46E-05mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: naphtho(2,3-b)furan-4,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: naphtho(2,3-b)furan-4,9-dione(5656-82-6)
• EPA Substance Registry System: naphtho(2,3-b)furan-4,9-dione(5656-82-6)

Safety Data

• Hazardous Substances Data: 5656-82-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H6O3/c13-10-7-3-1-2-4-8(7)11(14)12-9(10)5-6-15-12/h1-6H

Upstream product

• 159618-37-8 2-(3-furanoyl)benzoic acid 
• 75-36-5 acetyl chloride 
• 92487-47-3 4-acetoxynaphtho<2,3-b>furan 
• 32013-78-8 2,3-dihydronaphtho[2,3-b]furan-4,9-dione 
• 189763-01-7 4,9-dimethoxynaphthalene[2,3-b]furan 
• 133700-94-4 2-Ethoxy-2,3-dihydronaphtho<2,3-b>furan-4,9-dione 
• 478159-15-8 2-phenylsulfanyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 7193-15-9 2,3-dihydronaphtho[2,3-b]furan 
• 294840-65-6 2,3-dihydro-naphtho[2,3-b]furan-9-carbaldehyde 
• 294840-56-5 2,3-dihydro-naphtho[2,3-b]furan-9-ol 
• 294840-60-1 4,9-dimethoxy-2,3-dihydro-naphtho[2,3-b]furan 
• 294840-58-7 9-methoxy-2,3-dihydro-naphtho[2,3-b]furan-4-carbaldehyde 
• 294840-59-8 9-methoxy-2,3-dihydro-naphtho[2,3-b]furan-4-ol 

Downstream Products

• 83280-65-3 2-acetylnaphtho[2,3-b]furan-4,9-quinone 
• 1240306-61-9 (Z)-N-{(Z)-4-[4-(trifluoromethyl)phenylimino]-naphtho[2,3-b]furan-9(4H)-ylidene}-4-(trifluoromethyl)-benzenamine 
• 1240306-59-5 (Z)-N-[(Z)-9-(p-tolylimino)naphtho[2,3-b]furan-4(9H)-ylidene]-4-methyl-benzenamine 
• 1240306-58-4 (Z)-N-[(Z)-9-(4-chlorophenylimino)naphtho[2,3-b]furan-4(9H)-ylidene]-4-chlorobenzenamine 
• 1240306-60-8 (Z)-N-[(Z)-9-(4-methoxyphenylimino)naphtho[2,3-b]furan-4(9H)-ylidene]-4-methoxybenzenamine 
• 1240306-62-0 (Z)-N-[(Z)-4-(4-nitrophenylimino)naphtho[2,3-b]furan-9(4H)-ylidene]-4-nitro benzenamine 
• 1240306-54-0 (Z)-4-(phenylimino)naphtho[2,3-b]furan-9(4H)-one 
• 1240306-56-2 (Z)-N-((Z)-4-(phenylimino)naphtho[2,3-b]furan-9(4H)-ylidene)benzenamine 
• 1240306-55-1 (Z)-4-(4-fluorophenylimino)naphtho[2,3-b]furan-9(4H)-one 
• 1240306-57-3 (Z)-N-[(Z)-9-(4-fluorophenylimino)naphtho[2,3-b]furan-4(9H)-ylidene]-4-fluorobenzenamine 
• 1240306-63-1 bis(2-(diethylamino)ethyl) 4,4'-(1Z,1'Z)-naphtho[2,3-b]furan-4,9-diylidenebis(azan-1-yl-1-ylidene)dibenzoate 
• 1393549-74-0 C₂₁H₁₆O₄ 
• 676158-78-4 2-benzoyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 
• 1393549-95-5 C₂₃H₁₆O₆ 

Relevant articles and documents

Synthesis, biological evaluation and molecular docking of avicequinone C analogues as potential steroid 5α-reductase inhibitors

Avicequinone C (5a), a furanonaphthoquinone isolated from the Thai mangrove Avicennia marina has been shown previously to have interesting steroid 5α-reductase type 1 inhibitory activity. In this study, a series of avicequinone C analogues containing furanonaphthoquinone with different degrees of saturation and substituents at the furan ring were synthesized. The resulting synthetic avicequinone C and analogues (5a-f) along with some related compounds including 2,5-dihydroxy-1,4-benzoquinone (6) and natural naphthoquinones such as lawsone (7a) and lapachol (7b) were evaluated for their in vitro cell viability and steroid 5α-reductase type 1 inhibitory activities using the cultured cell line of human keratinocytes (HaCaT). This cell-based bioassay was performed based on a direct detection of the enzymatic product dihydrotestosterone (2) by using a non-radioactive high performance thin layer chromatography (HPTLC) method. Among the furanonaphthoquinones in this series, 5e having a propionic substituent at furan ring possessed approximately 22-fold more potent than the original isolated compound 5a. However, the compounds without furan motif such as 6, 7a and b could not inhibit the activity of steroid 5α-reductase. Molecular docking results of the in silico three-dimensional steroid 5α-reductase type 1-reduced nicotinamide adenine dinucleotide phosphate (NADPH) binary complex was performed via AutoDock Vina and it illustrated that the furanonaphthoquinone moiety and the substituent at furan ring might play a key role as pharmacophores for the steroid 5α-reductase inhibitory activity.

Base-Mediated Cyclization Reaction of 2-(5-Hydroxy-1-pentynyl)benzonitriles to 4-Amino-2,3-dihydronaphtho[2,3-b]furanes and Synthesis of Furanonaphthoquinones

An efficient transformation of 2-(5-hydroxy-1-pentynyl)benzonitriles 5 to furanonaphthoquinones 11 is presented. Treatment of 5 with 1.5 equiv of NaOMe in DMSO at 140 °C for 0.5 h gave 6 in good yields. Conversion of 6 to 11 was carried out by oxidation of 6 with Fremy's salt and KH2PO4 in acetone and water, followed by dehydrogenation using palladium on charcoal in diphenylether at reflux temperature.

NOVEL ESTERS OF 4, 9-DIHYDROXY-NAPHTHO [2, 3-b] FURANS FOR DISEASE THERAPIES

The present invention discloses esters of 4,9-dihydroxy-naphtho[2,3-b]furans and methods of making and using the same. The present invention also discloses conversion of the esters into therapeutically active 4,9-dihydroxy-naphtho[2,3-b]furans in vivo. The present invention furthermore discloses pharmaceutical compositions comprising the esters of 4,9-dihydroxy-naphtho[2,3-b]furans for the treatment of various indications including proliferative diseases.