17951-19-8

Usage

Uses

Piscicidal agent.

InChI:InChI=1/C21H16O6/c1-23-16-7-12-5-13-9-25-21(22)20(13)19(14(12)8-17(16)24-2)11-3-4-15-18(6-11)27-10-26-15/h3-8H,9-10H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 79862-77-4 9-(1,3-benzodioxol-5-yl)-7-hydroxy-6-methoxynaphtho[2,3-c]furan-1(3H)-one 
• 131719-30-7 [(3S,4R)-4-(Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-5-oxo-tetrahydro-furan-3-yl]-(tert-butyl-dimethyl-silanyloxy)-(3,4-dimethoxy-phenyl)-acetonitrile 
• 86431-57-4 2,3-bis-(hydroxymethyl)-6,7-dimethoxy-1-(3',4'-methylenedioxyphenyl)naphthalene 
• 131701-97-8 (9R,9aS)-9-Benzo[1,3]dioxol-5-yl-6,7-dimethoxy-1-oxo-1,3,9,9a-tetrahydro-naphtho[2,3-c]furan-4-carbonitrile 
• 28982-10-7 9-(benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one 
• 96264-86-7 6,7-Dimethoxy-1-(3,4-methylendioxyphenyl)-naphthalin-2,3-dicarbonsaeureanhydrid 
• 289622-34-0 6,7-dimethoxy-1-(benzo[1,3]dioxol-5-yl)naphthalene-2,3-dicarboxylic acid 2-ethyl ester 
• 52806-46-9 1-bromo-4,5-dimethoxy-2-methylbenzene 
• 126496-62-6 3,4-Dimethoxy-6-methylphenyl 3,4-methylenedioxyphenyl ketone 
• 172376-01-1 3,4-Dimethoxy-6-methylphenyl(3,4-methylenedioxyphenyl)methanol 
• 42923-54-6 α-piperonylidene-β-veratralidenesuccinic anhydride 
• 120-57-0 piperonal 
• 131701-93-4 α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile 

Relevant academic research and scientific papers

A Regiocontrolled Synthesis of Some Arylnaphthalide Lignans

Three arylnaphthalide lignans are synthesised by regiocontrolled transformations of Diels-Alder adducts generated from dimethyl acetylenedicarboxylate and suitable isobenzofurans.

ARYLNAPHTHALENE LIGNANS OF Haplophyllum dauricum. THE STRUCTURE OF DAURINOL

The arylnaphthalene lignans justicidin B and daurinol I have been isolated from the epigeal part of Haplophyllum dauricum (L.) G.Don.

The efficient synthesis and biological evaluation of justicidin B

A facile new synthetic method for the preparation of a Type-A 1-arylnaphthalene lactone skeleton was developed and used to synthesise justicidin B and several derivatives. Key synthesis steps included Hauser–Kraus annulation of a phthalide intermediate and Suzuki–Miyaura cross coupling between a triflated naphthalene lactone intermediate and various potassium organotrifluoroborates. With two exceptions, the derivatives showed significant inhibitory effect on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophages. Moreover, several compounds, including justicidin B, had marked cytotoxicity towards six human tumour cell lines.

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.

Patentiflorin A Analogs as Antiviral Agents

The present disclosure relates to patentiflorin A analogs that are useful as antivirals, such as anti-HIV, anti-coronaviral, anti-Ebola viral, and anti-influenza viral agents and methods of use thereof.

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.

JUSTICIDIN B DERIVATIVES OF ARYLNAPHTHALENE LIGNAN STRUCTURE AND METHOD FOR PRODUCING THE SAME

The present invention relates to a novel manufacturing method of an aryl naphthalene lignan compound. For the aryl naphthalene lignan-type compound and derivative synthesis of the present invention, a naphthalene skeleton center is built at first and an a

Intramolecular dehydro-diels-alder reaction affords selective entry to arylnaphthalene or aryldihydronaphthalene lignans

Intramolecular dehydro-Diels-Alder (DDA) reactions are performed affording arylnaphthalene or aryldihydronaphthalene lactones selectively as determined by choice of reaction solvent. This constitutes the first report of an entirely selective formation of arylnaphthalene lactones utilizing DDA reactions of styrene-ynes. The synthetic utility of the DDA reaction is demonstrated by the synthesis of taiwanin C, retrohelioxanthin, justicidin B, isojusticidin B, and their dihydronaphthalene derivatives. Computational methods for chemical shift assignment are presented that allow for regioisomeric lignans to be distinguished.

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