14944-34-4

Usage

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

• 81410-42-6 3,4-dihydro-3-hydroxymethyl-6,7-methylenedioxy-1-(3,4-methylenedioxyphenyl)naphthalene-2-carboxylic acid lactone 
• 32502-05-9 6,7-methylenedioxy-1-(3,4-methylenedioxyphenyl)naphthalene-2,3-dicarboxylic anhydride 
• 1002130-59-7 C₂₁H₁₁F₃O₉S 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 147771-00-4 5-<2-(Trimethylsilyl)ethenyl>-1,3-benzodioxole 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 10231-46-6 3-(benzo[d][1,3]dioxol-5-yl)propiolic acid 
• 71616-32-5 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 3-(benzo[d][1,3]dioxol-5-yl)propiolate 
• 164524-65-6 C₂₄H₂₂O₉S 
• 164524-66-7 5-benzo<1,3>dioxol-5-yl-8-(ethylthio)naphtho<2,3-d><1,3>dioxole-6,7-dicarboxylic acid dimethyl ester 
• 164524-63-4 benzo<1,3>dioxol-5-yl-<6-<(ethylthio)methyl>benzo<1,3>dioxol-5-yl>methanol 
• 176983-13-4 benzo<1,3>dioxol-5-yl-<6-<(ethylsulfinyl)methyl>benzo<1,3>dioxol-5-yl>methanone 
• 164524-64-5 benzo<1,3>dioxol-5-yl-<6-<(ethylthio)methyl>benzo<1,3>dioxol-5-yl>methanone 

Relevant academic research and scientific papers

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.

An insight into the t-butylbromide - Dimethyl sulfoxide reagent: A novel application in lignan total synthesis

A novel aromatisation sequence initiated by the t-butylbromide - dimethyl sulfoxide reagent is presented. The unprecedented conversion of the dithianes 1 and 3 to the aryl sulfides 6 and 7 has lead to the synthesis of the naturally occuring 9-deoxyarylnap

Justicia lignans v. three new β-apolignans from Justicia neesii ramamoorthy

The isolation and characterization of three new β-apolignans, namely, 1,4-dihydrotaiwanin C (3), jusneesiin (4) and jusneesiinol (5), in addition to (-) hibalactone (6), from J. neesii are reported. Compounds 4 and 5 are unprecedentedly angularly fused β-apolignans and the structure of 5 was confirmed by X-ray diffraction data.

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, synthesis, and in vitro antiplatelet aggregation activities of taiwanin C

Total synthesis of taiwanin C was realised efficiently in a global yield of 52%. Taiwanin C in aggregation assays inhibited platelet aggregation in a concentration-dependent manner with an IC50 of 0.46 μM after exposure of human platelet to AA. Similarly, to AA, taiwanin C inhibited significantly TRAP-6-induced platelet aggregation with IC50 of 0.56 μM. Molecular docking studies were carried out using the molecular target the COX-1, COX-2 and PAR-1 proteins. These studies suggest that taiwanin inhibits COX-1 more strongly than COX-2. Taiwanin C showed better antiplatelet action in the presence of TRAP-6 than indomethacin and molecular docking studies suggest different mechanisms of action for the two compounds on PAR-1. These results demonstrate that taiwanin C acts very efficiently in two different signaling pathways of platelet aggregation. Although preliminary, these results indicate that taiwanin C has potential for further studies on its use for the development of new antiplatelet.

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.

Rapid continuous photoflow synthesis of naturally occurring arylnaphthalene lignans and their analogs

Naturally occurring arylnaphthalene lignans (ANLs) are subclass of lignans in many dietary or medicinal plants. The progressing interest of ANLs is due to their diversified biological activities. Herein, we developed a convenient method for the preparation of naturally occurring ANLs and their analogs through the continuous photoflow intramolecular Diels–Alder reaction in several minutes under mild conditions with good yields and regioselectivities.

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).

Intramolecular dehydro-diels-alder reaction affords selective entry to arylnaphthalene or aryldihydronaphthalene lignans

Intramolecular dehydro-Diels-Alder (DDA) reactions are performed affording arylnaphthalene or aryldihydronaphthalene lactones selectively as determined by choice of reaction solvent. This constitutes the first report of an entirely selective formation of arylnaphthalene lactones utilizing DDA reactions of styrene-ynes. The synthetic utility of the DDA reaction is demonstrated by the synthesis of taiwanin C, retrohelioxanthin, justicidin B, isojusticidin B, and their dihydronaphthalene derivatives. Computational methods for chemical shift assignment are presented that allow for regioisomeric lignans to be distinguished.

Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles

Tandem reaction of 2-alkynylbenzonitriles with a Reformatsky reagent turned out to be a novel and efficient approach toward 1-aminonaphthalene-2- carboxylates. Interestingly, with 2-(3-hydroxyprop-1-ynyl)benzonitriles as the substrates, a more sophisticat