145726-16-5

Basic information

• Product Name: Naphtho[2,3-c]furan-1(3H)-one, 6,7-dimethoxy-9-(4-methoxyphenyl)-
• CAS NO: 145726-16-5
• Molecular Formula: C21H18O5
• Molecular Weight: 350.371
• Mol File: 145726-16-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 575.8±50.0 °C(Predicted)
• Density: 1.262±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Naphtho[2,3-c]furan-1(3H)-one, 6,7-dimethoxy-9-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphtho[2,3-c]furan-1(3H)-one, 6,7-dimethoxy-9-(4-methoxyphenyl)-(145726-16-5)
• EPA Substance Registry System: Naphtho[2,3-c]furan-1(3H)-one, 6,7-dimethoxy-9-(4-methoxyphenyl)-(145726-16-5)

Safety Data

• Hazardous Substances Data: 145726-16-5(Hazardous Substances Data)

Upstream product

• 76885-59-1 dimethyl 1-hydroxy-6,7-dimethoxynaphthalene-2,3-dicarboxylate 
• 76885-49-9 dimethyl 6,7-dimethoxy-1,4-dihydro-1,4-epoxynaphthalene-2,3-dicarboxylate 
• 531-88-4 5,6-dimethoxyphthalide 
• 1621253-02-8 2-formyl-4,5-dimethoxy-N,N-dimethylbenzamide 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 93-07-2 Veratric acid 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 1276122-32-7 C₂₁H₂₀O₄ 

Relevant articles and documents

Design and synthesis of arylnaphthalene lignan lactone derivatives as potent topoisomerase inhibitors

Background: Arylnaphthalene lignan lactones are a class of natural products containing the phenyl-naphthyl skeleton. Some arylnaphthalene lignan lactones have been used in clinical practice as antitumor agents, due to their cytotoxicity and inhibitory activities against DNA topoisomerase I (Topo I) and topoisomerase II (Topo II). Objective: This study presents the design and synthesis of arylnaphthalene lignan lactones derivatives. The inhibitory activities against Topo I and Topo IIα and antitumor activities of these compounds were assayed. Methods: A series of arylnaphthalene lignan lactones derivatives have been designed and synthesized, using the Diels-Alder reaction and Suzuki reaction as the key steps. Their antiproliferation activities were evaluated by sulforhodamine B assay on human breast cancer MDAMB-231, MDA-MB-435 and human cervical cancer HeLa cells. DNA relaxation assays were employed to examine the inhibitory activity of compounds 1-22 on Topo I and Topo IIα in vitro. Flow cytometry analysis was performed to study the drug effects on cell cycle progressions. Results: Seven compounds exhibited the modest anti-proliferation activity with IC50 values between 1.36 and 20 μM. Compounds 3, 19 and 22 showed potent inhibitory activities with IC50 values less than 1 μM. DNA relaxation assay revealed that compound 22 showed potent inhibitory activity against Topo IIα in vitro. Compound 22 also induced DNA breaks in MDA-MB-435 cells evidenced by comet tails and the accumulation of γ-H2AX foci. The ability of 22 in inducing DNA breaks mediated by Topo IIα resulted in G2/M phase arrest and apoptosis. Conclusion: This work indicates that arylnaphthalene lignan lactones derivatives represent a novel type of Topo IIα inhibitory scaffold for developing new antitumor chemotherapeutic agents.

A Garratt-Braverman route to aryl naphthalene lignans

A series of aryl naphthalene lignans were prepared in good yields starting from substituted bis-propargyl ethers. The method involved a base-mediated Garratt-Braverman cyclization followed by benzylic oxidation to the lactone. The chemoselectivity in the