82001-16-9

Upstream product

• 78473-72-0 3-(3,4-dimethoxybenzyl)-4-<3,4-methylenedioxy-α,α-bis(phenylthio)behzyl>butyrolactone 
• 86431-57-4 2,3-bis-(hydroxymethyl)-6,7-dimethoxy-1-(3',4'-methylenedioxyphenyl)naphthalene 
• 96264-86-7 6,7-Dimethoxy-1-(3,4-methylendioxyphenyl)-naphthalin-2,3-dicarbonsaeureanhydrid 
• 54370-00-2 2-bromo-4,5-dimethoxybenzyl alcohol 
• 124-38-9 carbon dioxide 
• 4302-52-7 4-ethynylveratrole 
• 1228103-79-4 3,4-methylenedioxyphenylpropargyl chloride 
• 1453191-44-0 1,6,7-trimethoxy-9-(3,4-methylenedioxy)phenylnaphtho[2,3-c]furan 
• 531-88-4 5,6-dimethoxyphthalide 
• 76885-49-9 dimethyl 6,7-dimethoxy-1,4-dihydro-1,4-epoxynaphthalene-2,3-dicarboxylate 
• 95436-24-1 dimethyl 1-(benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxynaphthalene-2,3-dicarboxylate 
• 76885-59-1 dimethyl 1-hydroxy-6,7-dimethoxynaphthalene-2,3-dicarboxylate 
• 93-07-2 Veratric acid 
• 225517-03-3 6,7-dimethoxy-2-(methoxycarbonyl)-1-(3,4-methylenedioxyphenyl)naphthalene-3-carboxylic acid 

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.

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.

Concise synthesis of arylnaphthalene lignans by regioselective intramolecular anionic diels-alder reactions of 1,7-diaryl-1,6-diynes

Total synthesis of phyllamycin A and C, justicidin B, and retrojusticidin B from simple arylalkynyl alcohols and (3,4-methylenedioxyphenyl)propynal was accomplished in 4-5 steps by employing an intramolecular anionic Diels-Alder reaction as the key step.

Palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes: Synthesis of justicidin B and retrojusticidin B

A facile synthesis of natural and unnatural arylnaphthalenes has been demonstrated via the unprecedented palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes using the N-heterocyclic carbene as a ligand. The unsymmetr

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.

Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of unsymmetrically substituted α-arylnaphthalenes: Application to total synthesis of natural lignan lactones

(Chemical Equation Presented) An efficient synthesis of highly substituted α-arylnaphthalene analogues has been developed utilizing Lewis acid-promoted regiocontrolled benzannulation of aryl(aryl′)-2,2- dichlorocyclopropylmethanols (aryl ≠ aryl′; abbrevia

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.

Total syntheses of justicidin B and retrojusticidin B using a tandem Horner-Emmons-Claisen condensation sequence

Short syntheses of justicidin B 1 and retrojusticidin B 4 are reported. The key feature is a new annulation reaction, involving a base induced union of ketoaldehyde 2 and phosphonate 3, that is used to construct the highly substituted naphthalene core.

Hindered rotation in arylnaphthalene lignans

Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.

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).