27792-97-8

Upstream product

• 32502-06-0 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-methylenedioxyphenyl)naphthalene 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 42123-31-9 5-benzo<1,3>dioxol-5-ylnaphtho<2,3-d><1,3>dioxole-6,7-dicarboxylic acid dimethyl ester 
• 1346682-47-0 1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(benzo[d][1,3]dioxol-5-yl)prop-2-ynyloxy)propan-2-one 
• 1346682-61-8 1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(benzo[d][1,3]dioxol-5-yl)prop-2-ynyloxy)propan-2-ol 
• 1346682-56-1 5-(3-(oxiran-2-ylmethoxy)prop-1-ynyl)benzo[d][1,3]dioxole 
• 6258-37-3 <3,4-(methylenedioxy)phenyl>propargyl alcohol 
• 57238-86-5 5-benzo[1,3]dioxol-5-yl-6,8-dihydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 124-38-9 carbon dioxide 
• 1228103-79-4 3,4-methylenedioxyphenylpropargyl chloride 
• 164524-67-8 5-benzo<1,3>dioxol-5-ylnaphtho<2,3-d><1,3>dioxole-6,7-dicarboxylic acid 6-methyl ester 

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.

Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation

An intramolecular approach to generate compounds containing an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl3 in combination with AgSbF6 works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and retrojusticidin B (Figure presented).

A Garratt-Braverman route to aryl naphthalene lignans

A series of aryl naphthalene lignans were prepared in good yields starting from substituted bis-propargyl ethers. The method involved a base-mediated Garratt-Braverman cyclization followed by benzylic oxidation to the lactone. The chemoselectivity in the

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.

Novel method for the synthesis of α- and β-halogenonaphthalenes by regioselective benzannulation of aryl(gem-dihalogenocyclopropyl)methanols: Application to the total synthesis of the lignan lactones, justicidin E and taiwanin C

Acid treatment of two types of aryl(gem-dihalogenocyclopropyl)methanols (ADCMs) 1 and 3 gives α- and β-halogenonaphthalenes in good yields with excellent selectivity. These alternative annulations involve two distinctive types of highly regioselective acid-induced cyclopropane ring cleavage, wherein the preferential formation of more stable cationic intermediates determines the selectivity. The stereochemical mode of both the preparation and the annulation between diastereoisomers of an ADCM has been checked. As a demonstration of this annulation, a total synthesis of each of the natural lignan lactones, justicidin E 19 and taiwanin C 20, has also been performed. Since these 4-arylnaphthalenes are expected to exhibit biological activity, the anti-platelet activating factor (anti-PAF) activity of justicidin E has been assayed.

Tandem Pummerer-Diels-Alder reaction sequence. A novel cascade process for the preparation of 1-arylnaphthalene lignans

The α-thiocarbocation generated from the Pummerer reaction of an o-benzoyl-substituted sulfoxide is intercepted by the adjacent keto group to produce an α-thio isobenzofuran as a transient intermediate which undergoes a subsequent Diels-Alder cycloadditio

A novel synthesis of α- and β-halonaphthalenes via regioselective ring cleavage of aryl(gem-dihalocyclopropyl)methanols and its application to total synthesis of lignan lactones, justicidin e and taiwanin c

Acid treatment of two types of aryl(gem-dihalocyclopropyl)methanols (ADCM) 1 gave α- and β-halonaphthalenes in good yields with excellent selectivity. With the new method used as the key step, the two title natural lignan lactones were synthesized in seve

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).