42923-60-4

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 
• 66130-44-7 1-(3',4'-Dimethoxyphenyl)-6,7-methylene-dioxynaphthalene-2,3-dicarboxylic acid 
• 42923-54-6 α-piperonylidene-β-veratralidenesuccinic anhydride 
• 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 
• 473253-65-5 3,4-dimethoxybenzyl-(6-formylbenzo[1,3]dioxol-5-yl)methanone 
• 5707-96-0 retrochinensin 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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 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.

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.

Synthetic experiments in Lignans: Part IX - Thermal and

Thermal and photochemical cyclisations of some dibenzylidenesuccinic anhydrides (Ia to Ic) lead to the formation of a mixture of 1-phenylnaphthalene anhydrides.Blocking one of the cyclisable positions in any one of the two aryl nuclei by bromine atom shows no regiospecificity in directing cyclisation into the non-halogenated aryl nucleus either during thermal or photochemical cyclisation.Cyclisation even into the halogenated aromatic nucleus itself, expected to be stereoselective, is nonstereoselective.The products are preferentially formed by elimination of HBr rather than H2.Incidentally, the naphthalene analogue (VI) of lintetralin, a natural tetralin from Phyllanthus niruri and the respective partial monomethyl ethers (Vm and Vn) have been prepared and characterised by their PMR spectra.

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.