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

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

• 98449-77-5 5-(3,4-Dimethoxy-phenyl)-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid 7-methyl ester 
• 42923-54-6 α-piperonylidene-β-veratralidenesuccinic anhydride 
• 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 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 6120-26-9 6-bromobenzo[d][1,3]dioxole-5-carbonitrile 
• 66130-46-9 dimethyl 6,7-methylenedioxy-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylate 
• 124-38-9 carbon dioxide 
• 4302-52-7 4-ethynylveratrole 
• 1228103-79-4 3,4-methylenedioxyphenylpropargyl chloride 
• 162285-53-2 diisopropyl 5-methoxynaphtho<2,3-d>-1,3-dioxole-6,7-dicarboxylate 
• 162285-55-4 6-(isopropyloxycarbonyl)-5-methoxynaphtho<2,3-d>-1,3-dioxole-7-carboxylic acid 
• 162285-56-5 isopropyl 7-hydroxymethyl-5-methoxynaphtho<2,3-d>-1,3-dioxole-6-carboxylate 

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.

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.

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

Silver-catalyzed one-pot synthesis of arylnaphthalene lactone natural products

Naturally occurring arylnaphthalene lactone lignans have demonstrated a variety of valuable medicinal chemistry properties and have therefore been of continued interest to drug discovery research. Our group has demonstrated a silver-catalyzed one-pot synthesis of the arylnaphthalene lactone core using carbon dioxide, phenylpropargyl chloride, and phenylacetylene. This new approach has been employed in the synthesis of six arylnaphthalene lactone natural products: retrochinensin (1), justicidin B (2), retrojusticidin B (3), chinensin (4), justicidin E (5), and taiwanin C (6). Additionally, an arylnaphthalene lactone regioisomer was isolated (9), which we refer to as isoretrojusticidin B.

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.

Studies on disease-modifying antirheumatic drugs. III. Bone resorption inhibitory effects of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4- triazol-1-ylmethyl)quinoline-3-carboxylate (TAK-603) and related compounds

In the course of our studies aimed at obtaining new drugs for treatment of bone and joint diseases, chemical modification of the potent bone resorption inhibitors justicidins, was performed and various naphthalene lactones, quinoline lactones and quinoline derivatives bearing an azole moiety at the side chain were prepared. Their inhibitory effects on bone resorption were evaluated by Raisz's method, and several compounds, including ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1- ylmethyl)quinoline-3-arboxylate (6c, TAK-603), were found to have activities comparable with or superior to the justicidins. The 4-(3-isopropoxy-4- methoxy)phenyl derivative (6d), in particular, displayed a marked increase in potency. TAK-603 and compound 6d were very effective in preventing osteoclast formation and bone resorption by mature osteoelasts. Further, TAK-603 was shown to be effective in preventing bone loss in ovariectomized mice.

Facila Construction of the 1-Phenylnaphthyl Skeleton via an Ester-mediated Nucleophilic Aromatic Substitution Reaction. Applications to the Synthesis of Phenylnaphthalide Lignans

A convenient method is presented for the construction of the 1-phenylnaphthyl skeleton via an ester-mediated nucleophilic displacement of a methoxy group from an aromatic nucleus by Grignard nucleophiles.Thus, treatment of isopropyl 1-methoxy-2-naphthoate

Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins

1-Arylnaphthalene lignan lactones were synthesized in good yields from O-(tert-butyldimethylsilyl)cyanohydrins in two steps based on a conjugate addition-aldol reaction, followed by acid-catalyzed closure to form the naphthalene ring. 4-Hydroxy-1-arylnaph

Synthetic Experiments in Lignans: Part XI - Use of Pyridinium Chlorochromate as a Regioselective Reagent in the Synthesis of 1-Phenylnaphthalene Lactones

Pyridinium chlorochromate has been found to be a regioselective reagent in the oxidation of 2,3-bis(hydroxymethyl)-1-phenylnaphthalenes with preferential attack on 2-hydroxymethyl to yield normal lactones as the major products (>65percent).

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.