14944-34-4

Basic information

• Product Name: 6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one
• Synonyms: 5-(1,3-Benzodioxol-5-yl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(8H)-one;6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one;Taiwanin C
• CAS NO: 14944-34-4
• Molecular Formula: C20H12 O6
• Molecular Weight: 348.31
• Mol File: 14944-34-4.mol
• Article Data: 28

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one(14944-34-4)
• EPA Substance Registry System: 6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one(14944-34-4)

Safety Data

• Hazardous Substances Data: 14944-34-4(Hazardous Substances Data)

Usage

Description

6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one is a complex organic compound characterized by its unique chemical structure, which includes an epoxymethanoxy group, a benzodioxole ring, and a dihydronaphthofuranone core. This molecule exhibits a range of biological activities and potential applications across various industries due to its structural diversity and functional groups.

Uses

Used in Pharmaceutical Industry:
6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one is used as a pharmaceutical agent for its potential anticancer properties. The compound has been shown to selectively inhibit oral cancer cell proliferation via ERK1/2 inactivation, making it a promising candidate for the development of targeted cancer therapies.
Used in Chemical Synthesis:
In the field of chemical synthesis, 6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one can be utilized as a key intermediate or building block for the synthesis of more complex molecules with diverse applications. Its unique structure and functional groups make it a valuable component in the development of new drugs, materials, and other specialty chemicals.
Used in Material Science:
The compound's structural features and functional groups also make it a candidate for use in material science, where it could be employed in the development of novel materials with specific properties. These properties may include enhanced stability, improved mechanical strength, or unique optical, electronic, or magnetic characteristics.
Used in Research and Development:
6,7-(Epoxymethanoxy)-9-(1,3-benzodioxole-5-yl)-1,3-dihydronaphtho[2,3-c]furan-1-one is also used in research and development settings, where it can serve as a model compound for studying the effects of structural modifications on biological activity and other properties. This can help researchers better understand the structure-activity relationships of similar compounds and guide the design of more effective molecules for various applications.

Upstream product

• 32502-06-0 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-methylenedioxyphenyl)naphthalene 
• 75-09-2 dichloromethane 
• 164524-67-8 5-benzo<1,3>dioxol-5-ylnaphtho<2,3-d><1,3>dioxole-6,7-dicarboxylic acid 6-methyl ester 
• 6258-37-3 <3,4-(methylenedioxy)phenyl>propargyl alcohol 
• 1346682-56-1 5-(3-(oxiran-2-ylmethoxy)prop-1-ynyl)benzo[d][1,3]dioxole 
• 1346682-61-8 1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(benzo[d][1,3]dioxol-5-yl)prop-2-ynyloxy)propan-2-ol 
• 1346682-47-0 1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(benzo[d][1,3]dioxol-5-yl)prop-2-ynyloxy)propan-2-one 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 16167-42-3 C₁₂H₁₀O₄ 
• 84736-28-7 (methylenedioxy-3,4 benzylidene) α-hemisuccinate de methyle 
• 68970-49-0 7,7′-dihydrotaiwanin C 
• 42123-31-9 5-benzo<1,3>dioxol-5-ylnaphtho<2,3-d><1,3>dioxole-6,7-dicarboxylic acid dimethyl ester 
• 71616-32-5 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 3-(benzo[d][1,3]dioxol-5-yl)propiolate 
• 10231-46-6 3-(benzo[d][1,3]dioxol-5-yl)propiolic acid 

Relevant articles and documents

-

-

Arylnaphthalene lignans through Pd-catalyzed [2+2+2] cocyclization of arynes and diyness: Total synthesis of taiwanins C and E

3 in 1 : A novel method for the synthesis of the arylnaphthalene skeleton by the Pd0-catalyzed [2+2+2] cocyclization of diynes and arynes involves three C-C bond-forming reactions in a single step (see scheme; R = CON(OCH3)CH3, dba = dibenzylideneacetone). This cocyclization was the key step in the total synthesis of the arylnaphthalene lignans taiwanins C and E.

-

-

HIGHLY REGIOSELECTIVE LACTONE FORMATION CATALYZED BY RUTHENIUM COMPLEXES. AN APPLICATION TO SYNTHESIS OF ARYLNAPHTHALENE LIGNANS

Ruthenium catalyzed hydrogenation of cyclic anhydrides and dehydrogenation of diols have been successfully applied to the highly regioselective synthesis of arylnaphthalene lignans.

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.

Regioselective route for arylnaphthalene lactones: Convenient synthesis of taiwanin C, justicidin E, and daurinol

Arylnaphthalene lactones are natural products which can be isolated from a wide range of plants and have the significant biological activities including cytotoxicity, antimicrobial, diuretic, and ion channel blocking. The drawback of the previous intramolecular Diels-Alder reaction of 3-arylprop-2-ynyl 3-arylpropiolates was to generate two regioisomers of arylnaphthalene lactone without selectivity. Herein, we report a convenient and regioselective synthesis method in which the intramolecular Diels-Alder reaction of an arylalkene-arylalkyne and subsequent DDQ oxidation was used for Type I and Type II arylnaphthalene lactones, respectively. We demonstrated the synthesis of three lignans, taiwanin C (Type I), justicidin E (Type II), and daurinol (Type I and anti-cancer activity).