32013-78-8

Upstream product

• 294840-56-5 2,3-dihydro-naphtho[2,3-b]furan-9-ol 
• 406164-70-3 2-hydroxy-3-(2-hydroxyethyl)-1,4-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 7193-15-9 2,3-dihydronaphtho[2,3-b]furan 
• 1526990-22-6 2-(1,3,4-trimethoxynaphthalen-2-yl)-ethanol 
• 60683-53-6 1,2,4-trimethoxynaphthalene 
• 294840-59-8 9-methoxy-2,3-dihydro-naphtho[2,3-b]furan-4-ol 
• 294840-58-7 9-methoxy-2,3-dihydro-naphtho[2,3-b]furan-4-carbaldehyde 
• 294840-65-6 2,3-dihydro-naphtho[2,3-b]furan-9-carbaldehyde 
• 198958-09-7 2-(ethylacetate)-3-hydroxy-1,4-naphthoquinone 
• 294840-60-1 4,9-dimethoxy-2,3-dihydro-naphtho[2,3-b]furan 

Downstream Products

• 5656-82-6 naphtho[2,3-b]furan-4,9-dione 

Relevant academic research and scientific papers

Novel synthesis of linear furonaphthoquinones

An efficient synthesis of naturally occurring and biologically active furonaphthoquinones is described starting from suitably substituted dihydronaphthofurans.

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.

Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4- trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone

The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4- trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4- trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield.

Potent antitumor activity of synthetic 1,2-naphthoquinones and 1,4-naphthoquinones

Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG2) with IC50 values of 0.92-9.63 μM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC50 values of 7.61-24.13 μM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with similar cytotoxicity as 1,2-pyranonaphthoquinones. In comparison to 1,2-naphthoquinones, six 1,4-naphthoquinones derivatives fused with pyran ring (8-10) and furan ring (11-13) were synthesized and they showed less cytotoxicity or inactive to the cancer cell lines. Moreover, compound 13 had significant cytotoxicity against HeLa cell line (IC50 value of 9.25 μM) while it showed no toxic to vero cell.