5707-96-0

Basic information

• Product Name: Justicidin B
• Synonyms: 9-(3,4-dimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one;UNII-RQQ8T34V5F;9-(3,4-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8h)-one;Retrochinensin;Retrochinesin
• CAS NO: 5707-96-0
• Molecular Formula: C₂₁H₁₆O₆
• Molecular Weight: 364.354
• Mol File: 5707-96-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 593.2°Cat760mmHg
• Flash Point: 262.2°C
• Density: 1.376g/cm³
• CAS DataBase Reference: Justicidin B(CAS DataBase Reference)
• NIST Chemistry Reference: Justicidin B(5707-96-0)
• EPA Substance Registry System: Justicidin B(5707-96-0)

Safety Data

• Hazardous Substances Data: 5707-96-0(Hazardous Substances Data)

Usage

General Description

Justicidin B is a natural chemical compound found in the roots of the Justicia herb, which is known for its medicinal properties. It belongs to the class of phytosterols and has been found to possess anti-inflammatory and anti-cancer properties. Studies have shown that Justicidin B has the ability to inhibit the growth of cancer cells and induce apoptosis, making it a promising candidate for cancer therapy. Additionally, it has also been investigated for its potential in treating inflammatory conditions such as arthritis. Justicidin B's pharmacological properties make it a valuable chemical for research and drug development.

Synthetic route

4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone (103844-18-4, 118626-89-4) → retrochinensin (5707-96-0)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform; benzene for 48h; Heating;	100%

2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene (42923-60-4) → retrochinensin (5707-96-0)

Conditions	Yield
With 1-Phenylbut-1-en-3-one; dihydridotetrakis(triphenylphosphine)ruthenium In toluene for 10h; Heating;	94%
With manganese(IV) oxide In dichloromethane at 20℃; for 48h;	91%

2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene (42923-60-4) → 1-(3,4-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxynaphthalene-2-carboxylic acid lactone (31888-76-3) + retrochinensin (5707-96-0)

Conditions	Yield
With barium permanganate In dichloromethane at 20℃; for 48h;	A 19% B 80%
With bis(pyridine)silver permanganate In benzene for 2h; Heating;	A 18.2% B 56.6%
With pyridinium chlorochromate In chloroform for 12h; Ambient temperature;	A 53.2% B 25.3%
With silica gel; silver carbonate In benzene for 3h; Heating;	A 14 mg B 58 mg

6,7-methylenedioxy-1-(3,4-dimethoxyphenyl)naphthalene-2,3-dicarboxylic acid 2-ethyl ester (289622-32-8) → retrochinensin (5707-96-0)

Conditions	Yield
With lithium borohydride; sodium hydride In tetrahydrofuran; 1,4-dioxane for 28h; Heating;	72%

α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone (72622-61-8) → retrochinensin (5707-96-0)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 24h; Heating;	70%

erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone (103844-12-8) → retrochinensin (5707-96-0)

Conditions	Yield
With trifluoroacetic acid for 2h; Heating;	62%
With trifluoroacetic acid	60%

C21H16O6 → justicidin B (17951-19-8) + retrochinensin (5707-96-0)

Conditions	Yield
In dichloromethane at 0℃; for 0.166667h; Diels-Alder Cycloaddition; Flow reactor; Irradiation; regioselective reaction;	A 17.3% B 52.2%

1-(3',4'-dimethoxyphenyl)-6,7-methylenedioxynaphthalene-2,3-dicarboxylic anhydride (42923-53-5) → retrochinensin (5707-96-0)

Conditions	Yield
With sodium tetrahydroborate	49.5%

3,4-methylenedioxyphenylethyne (57134-53-9) + carbon dioxide (124-38-9) + 3,4-dimethoxyphenylpropargyl chloride (1184406-44-7) → justicidin B (17951-19-8) + retrochinensin (5707-96-0)

Conditions	Yield
With 18-crown-6 ether; silver(I) iodide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 5h; Molecular sieve;	A 16% B 16%

erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone (103844-12-8) → retrochinensin (5707-96-0) + threo-3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone (103865-35-6, 118917-44-5) + erythro-3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone (103865-35-6, 118917-44-5)

Conditions	Yield
With tin(IV) chloride In dichloromethane for 1h; Product distribution; Ambient temperature; attempted cyclisations of further derivatives with various acids;

3-(1',3'-benzodioxol-5'-ylmethylene)-4-(3'',4''-dimethoxybenzyl)dihydrofuran-2(5H)-one (50816-74-5) → retrochinensin (5707-96-0)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 24h; Heating;	16 mg

dimethyl 6,7-methylenedioxy-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylate (66130-46-9) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / -78 - 0 °C 2: 80 percent / BaMnO4 / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / -78 - 0 °C 2: 91 percent / MnO2 / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 220 mg / LiAlH4 / tetrahydrofuran / 6 h / Heating 2: 58 mg / silica gel - silver carbonate / benzene / 3 h / Heating View Scheme

3,4-dimethoxybenzyl-(6-formylbenzo[1,3]dioxol-5-yl)methanone (473253-65-5) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 53 percent / NaOMe / methanol; tetrahydrofuran / 3 h / 0 °C 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / -78 - 0 °C 3: 80 percent / BaMnO4 / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 53 percent / NaOMe / methanol; tetrahydrofuran / 3 h / 0 °C 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / -78 - 0 °C 3: 91 percent / MnO2 / CH2Cl2 / 48 h / 20 °C View Scheme

(3,4-dimethoxyphenyl)-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)methanol (473253-67-7) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / pyridinium chlorochromate; Al2O3 / CH2Cl2 / 0.5 h / 20 °C 2: 53 percent / NaOMe / methanol; tetrahydrofuran / 3 h / 0 °C 3: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / -78 - 0 °C 4: 80 percent / BaMnO4 / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 65 percent / pyridinium chlorochromate; Al2O3 / CH2Cl2 / 0.5 h / 20 °C 2: 53 percent / NaOMe / methanol; tetrahydrofuran / 3 h / 0 °C 3: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / -78 - 0 °C 4: 91 percent / MnO2 / CH2Cl2 / 48 h / 20 °C View Scheme

diethyl 6,7-methylenedioxy-1-(3,4-dimethoxyphenyl)naphthalene-2,3-dicarboxylate (289622-27-1) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / potassium trimethylsilanolate / tetrahydrofuran / 5 h / 20 °C 2: 72 percent / NaH; LiBH4 / dioxane; tetrahydrofuran; various solvent(s) / 28 h / Heating View Scheme

(S)-2-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-3-(3,4-dimethoxy-benzyl)-butane-1,4-diol (94285-09-3) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.0 mg / MnO2 / acetone / 20 h 2: 16 mg / DDQ / benzene / 24 h / Heating View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) + polymer-PPh2(1+)-CH3*I(1-) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / NaOMe / methanol / 2 h / Heating 2: 66 percent / Na, ethanol / 6 h / Ambient temperature 3: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 24 h / Heating View Scheme

(2E,3E)-3-(methoxycarbonyl)-2-((benzo[d][1,3]-dioxol-6-yl)methylene)-4-(3,4-dimethoxyphenyl)but-3-enoic acid (150715-15-4) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / Na, ethanol / 6 h / Ambient temperature 2: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 24 h / Heating View Scheme

α-piperonylidene-β-veratralidenesuccinic anhydride (42923-54-6, 53945-02-1, 91364-75-9) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 3 steps 2: 220 mg / LiAlH4 / tetrahydrofuran / 6 h / Heating 3: 58 mg / silica gel - silver carbonate / benzene / 3 h / Heating View Scheme

((3,4-dimethoxyphenyl)methylene)bis(phenylsulfane) (60354-22-5) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) BuLi / 1.) THF, - 78 deg C, 30 min; 2.) THF, -78 deg C, 90 min; 3.) THF, -78 deg C, 2 h 2: 62 percent / trifluoroacetic acid / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 2: 60 percent / TFA View Scheme

3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone (103865-35-6, 118917-44-5) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / NaBH4 / methanol / 4 h / 0 °C 2: 86 percent / BuLi / tetrahydrofuran / 2 h / -78 deg C to room temperature 3: 15 mg / K2CO3, FSO3Me / CH2Cl2 / 20 h / Ambient temperature 4: 100 percent / DDQ / benzene; CHCl3 / 48 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 95 percent / NaBH4 / methanol / 4 h / 0 °C 2: 50 percent / FSO3Me / CH2Cl2 / 18 h / Ambient temperature 3: 100 percent / DDQ / benzene; CHCl3 / 48 h / Heating View Scheme

erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-98-2, 118917-47-8, 144539-71-9) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 15 mg / K2CO3, FSO3Me / CH2Cl2 / 20 h / Ambient temperature 2: 100 percent / DDQ / benzene; CHCl3 / 48 h / Heating View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / HCl gas / CHCl3 / 1 h / 0 °C 2: 1.) BuLi / 1.) THF, - 78 deg C, 30 min; 2.) THF, -78 deg C, 90 min; 3.) THF, -78 deg C, 2 h 3: 62 percent / trifluoroacetic acid / 2 h / Heating View Scheme

erythro-3-(α-hydroxy-3'',4''-dimethoxybenzyl)-2-(3,4-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-97-1, 118917-46-7, 144539-70-8) → retrochinensin (5707-96-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / BuLi / tetrahydrofuran / 2 h / -78 deg C to room temperature 2: 15 mg / K2CO3, FSO3Me / CH2Cl2 / 20 h / Ambient temperature 3: 100 percent / DDQ / benzene; CHCl3 / 48 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 50 percent / FSO3Me / CH2Cl2 / 18 h / Ambient temperature 2: 100 percent / DDQ / benzene; CHCl3 / 48 h / Heating View Scheme

retrochinensin (5707-96-0) → 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene (42923-60-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 6h;	65%

Upstream product

• 72622-61-8 α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 50816-74-5 3-(1',3'-benzodioxol-5'-ylmethylene)-4-(3'',4''-dimethoxybenzyl)dihydrofuran-2(5H)-one 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 124-38-9 carbon dioxide 
• 1184406-44-7 3,4-dimethoxyphenylpropargyl chloride 
• 66130-46-9 dimethyl 6,7-methylenedioxy-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylate 
• 118825-97-1 erythro-3-(α-hydroxy-3'',4''-dimethoxybenzyl)-2-(3,4-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 118825-98-2 erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone 
• 103865-35-6 3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone 
• 60354-22-5 4-[Bis(phenylsulfanyl)methyl]-1,2-dimethoxybenzene 
• 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 
• 94285-09-3 (S)-2-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-3-(3,4-dimethoxy-benzyl)-butane-1,4-diol 

Downstream Products

• 42923-60-4 2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene 

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.

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 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.