5656-82-6

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 academic research and scientific papers

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.

Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents

Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.

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.

NAPHTHOQUINONES FOR DISEASE THERAPIES

The present invention discloses novel naphtho[2,3-b]furan-4,9-diones and naphtho[2,3-b]thiophene-4,9-diones and methods of making and using the same. The present invention also discloses pharmaceutical compositions comprising novel naphtho[2,3-b]furan-4,9

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.

NOVEL ANPHTHOQUINONES FOR DISEASE THERAPIES

Naphtho[2,3-b]furan-4,9-diones and naphtho[2,3-b]thiophene-4,9-diones, the preparation methods and uses thereof are disclosed. The pharmaceutical compositions comprising such compounds for the treatment of various indications including proliferative disea

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.

Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide

A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho-[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in vitro potency with IC50 values in the submicromolar range was attained with electron-withdrawing substituents, some compounds were found to induce plasma membrane damage, as evidenced by the release of LDH activity from cytoplasm of the keratinocytes. The most potent analogue against keratinocyte hyperproliferation was the 1,2,4-oxadiazole 18, the potency of which was combined with comparably low cytotoxic membrane damaging effects. Structure-activity relationship studies with either metabolically stable or labile analogues revealed that the quinone moiety was required for activity. Selected compounds were studied in detail for their capability to generate superoxide radicals both in isolated enzymatic one- and two-electron reduction assays as well as in a HaCaT cell-based assay.

Furo[3′,2′:3,4]naphtho[1,2-d]imidazole derivatives as potential inhibitors of inflammatory factors in sepsis

Synthesis and anti-inflammatory effects of certain furo[3′,2′:3,4]naphtho[1,2-d]imidazole derivatives 12-18 were studied. These compounds were synthesized from naphtho[1,2-b]furan-4,5-dione (10) which in turn was prepared from the known 2-hydoxy-1,4-napht

Facile synthesis of avicequinone-B natural product

An efficient synthesis of avicequinone-B (2) and furonaphthoquinone 4 has been carried out starting from 2-hydroxy-1,4-naphthoquinone (6) by CAN-mediated cycloaddition reaction.