42923-60-4

Basic information

• Product Name: 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene
• Synonyms: 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene
• CAS NO: 42923-60-4
• Molecular Weight: 368.386
• Mol File: 42923-60-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene(42923-60-4)
• EPA Substance Registry System: 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene(42923-60-4)

Safety Data

• Hazardous Substances Data: 42923-60-4(Hazardous Substances Data)

Upstream product

• 66130-46-9 dimethyl 6,7-methylenedioxy-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylate 
• 95436-24-1 dimethyl 1-(benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxynaphthalene-2,3-dicarboxylate 
• 5707-96-0 retrochinensin 
• 473253-65-5 3,4-dimethoxybenzyl-(6-formylbenzo[1,3]dioxol-5-yl)methanone 
• 66130-44-7 1-(3',4'-Dimethoxyphenyl)-6,7-methylene-dioxynaphthalene-2,3-dicarboxylic acid 
• 42923-54-6 α-piperonylidene-β-veratralidenesuccinic anhydride 
• 150715-15-4 (2E,3E)-3-(methoxycarbonyl)-2-((benzo[d][1,3]-dioxol-6-yl)methylene)-4-(3,4-dimethoxyphenyl)but-3-enoic acid 
• 72622-61-8 α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 126454-99-7 prasanthaline 
• 473253-67-7 (3,4-dimethoxyphenyl)-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)methanol 

Downstream Products

• 31888-76-3 1-(3,4-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxynaphthalene-2-carboxylic acid lactone 
• 5707-96-0 retrochinensin 

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 convenient total synthesis of (+/-)-jatrophan and 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)naphthalene, lignan constituents of Jatropha gossypifolia Linn.

Convenient synthetic routes to (+/-)-jatrophan and 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)naphthalene; the constituents of Jatropha gossypifolia Linn. have been reported.Stobbe condensation of piperonal with dimethyl succinate followed by methylation affords 4-(3',4'-methylenedioxyphenyl)-3-methoxy-carbonyl-methylbut-3-enoate.A second Stobbe condensation with veratraldehyde followed by Bouveault-Blanc reduction affords (+/-)-jatrophan.The aryl naphthalene lignan, 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)naphthalene, has been synthesised from jatrophan by oxidative cyclisation followed by lithium aluminum hydride reduction.

DDQ-Cyclodehydrogenation: Syntheses of 1-Phenylnaphthalenic Lignans

1,2-Diarylidenesuccinic anhydrides (Ia-c) when refluxed with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and dry HCl in anhyd. benzene undergo cyclization to give 1-phenylnaphthalene-2,3-dicarboxylic anhydrides (IIa-d) in 65-70percent yields.Starting from the anhydrides IIc and IId, syntheses of retochinensin (Vc), chinensin (VIc), retrojusticidin-B (Vd) and justicidin-B (VId) have been achieved.