31888-76-3

Basic information

• Product Name: Chinensin
• Synonyms: Chinensin;5-(3,4-Dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(8H)-one;6,7-(Epoxymethanoxy)-9-(3,4-dimethoxyphenyl)-1,3-dihydronaphtho[2,3-c]furan-1-one
• CAS NO: 31888-76-3
• Molecular Formula: C₂₁H₁₆O₆
• Molecular Weight: 364.35
• Mol File: 31888-76-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 220-222 °C
• Boiling Point: 594.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.376±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Chinensin(CAS DataBase Reference)
• NIST Chemistry Reference: Chinensin(31888-76-3)
• EPA Substance Registry System: Chinensin(31888-76-3)

Safety Data

• Hazardous Substances Data: 31888-76-3(Hazardous Substances Data)

Upstream product

• 42923-60-4 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene 
• 42923-53-5 1-(3',4'-dimethoxyphenyl)-6,7-methylenedioxynaphthalene-2,3-dicarboxylic anhydride 
• 98449-77-5 5-(3,4-Dimethoxy-phenyl)-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid 7-methyl ester 
• 162285-59-8 isopropyl 5-(3,4-dimethoxyphenyl)-7-(methoxymethoxymethyl)naphtho<2,3-d>-1,3-dioxole-6-carboxylate 
• 31786-43-3 1-(3,4-dimethoxyphenyl)-3,4-dihydro-3-hydroxymethyl-6,7-methylenedioxynaphthalene-2-carboxylic acid lactone 
• 289622-32-8 6,7-methylenedioxy-1-(3,4-dimethoxyphenyl)naphthalene-2,3-dicarboxylic acid 2-ethyl ester 
• 816462-34-7 3,4-dimethoxyphenylpropioloyl chloride 
• 42923-54-6 α-piperonylidene-β-veratralidenesuccinic anhydride 
• 124-38-9 carbon dioxide 
• 4302-52-7 4-ethynylveratrole 
• 1228103-79-4 3,4-methylenedioxyphenylpropargyl chloride 
• 1609162-54-0 6-(3-hydroxyprop-1-ynyl)benzo[d][1,3]dioxole-5-carbonitrile 
• 1609162-55-1 9-amino-6,7-methylenedioxynaphtho[2,3-c]furan-1(3H)-one 
• 1609162-56-2 9-iodo-6,7-methylenedioxynaphtho[2,3-c]furan-1(3H)-one 

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.

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

A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans

A new aromatic annulation reaction based on sequential Horner-Emmons and Claisen condensation reactions is described. The method is high yielding and provides a rapid entry to arylnaphthalenes. The lignan natural products justicidin B 1, retrojusticidin B 2, taiwanin C 3, justicidin E 4, chinensin 5 and retrochinensin 6 have all been synthesised in good overall yield using this protocol, demonstrating its potential in multiple parallel synthesis. The selective oxidation of diols 34-36 to the corresponding retrolactones with barium manganate(VI) is also noteworthy.