Production Method 1

18633-71-1

83280-65-3

Reaction Conditions

1.1 Reagents: Chromium trioxide Solvents: Acetic acid ,  Acetic anhydride

Reference

An easy approach to prepare naphtho[2,3-b]furan-4,9-diones

Ferreira, V. F.; et al, Synthetic Communications, 1989, 19(5-6), 1061-9

Production Method 2

318997-73-8

83280-65-3

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Benzene
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Efficient synthesis of cytotoxic furonaphthoquinone natural products

Lee, Yong Rok; et al, Synthetic Communications, 2001, 31(3), 381-386

Production Method 3

318997-73-8

83280-65-3

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Benzene ;  5 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents

Acuna, Julio; et al, Molecules, 2018, 23(1), 186/1-186/21

Production Method 4

83889-95-6

83280-65-3

Reaction Conditions

Reference

Furanonaphthoquinones from Tabebuia ochracea

Zani, Carlos L.; et al, Phytochemistry, 1991, 30(7), 2379-81

Production Method 5

83-72-7

61203-01-8

83280-65-3

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Tetrahydrofuran ;  2 °C; 40 min, 2 °C; 1 h, 2 °C → 22 °C
2.1 1 h

Reference

First-Generation Process Development of Napabucasin and the Impurity Control Strategy

Katz, Christopher E. ; et al, Organic Process Research & Development, 2023, 27(6), 1036-1052

Production Method 6

83-72-7

83280-65-3

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Dimethylformamide ;  0 °C
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Dimethylformamide ;  50 °C

Reference

Conjugates Derived from Lapatinib Derivatives with Cancer Cell Stemness Inhibitors Effectively Reversed Drug Resistance in Triple-Negative Breast Cancer

Wang, Yuanjiang; et al, Journal of Medicinal Chemistry, 2021, 64(17), 12877-12892

Production Method 7

117560-06-2

83280-65-3

Reaction Conditions

1.1 Catalysts: Copper oxide (Cu2O) ,  Palladium diacetate ,  Copper bromide (CuBr) Solvents: Pyridine ;  4 h, 80 °C
2.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  12 h, -10 °C

Reference

Synthesis and cytotoxicity on human leukemia cells of furonaphthoquinones isolated from Tabebuia plants

Inagaki, Ryuta; et al, Chemical & Pharmaceutical Bulletin, 2013, 61(6), 670-673

Production Method 8

318997-73-8

83280-65-3

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Benzene
1.2 Reagents: Ammonium chloride
1.3 Solvents: Ethyl acetate

Reference

Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products

Lee, Yong Rok; et al, Tetrahedron, 2000, 56(45), 8845-8853

Production Method 9

83889-95-6

83280-65-3

Reaction Conditions

1.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  12 h, -10 °C

Reference

Synthesis and cytotoxicity on human leukemia cells of furonaphthoquinones isolated from Tabebuia plants

Inagaki, Ryuta; et al, Chemical & Pharmaceutical Bulletin, 2013, 61(6), 670-673

Production Method 10

147568-55-6

83280-65-3

Reaction Conditions

1.1 Reagents: Manganese oxide (MnO2) Solvents: Methylcyclohexane

Reference

Domino Michael-O-alkylation reaction: one-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis

Hagiwara, Hisahiro; et al, Journal of the Chemical Society, 2001, (22), 2946-2957

Production Method 11

189763-03-9

83280-65-3

Reaction Conditions

1.1 Reagents: Ceric ammonium nitrate Solvents: Acetonitrile ,  Water

Reference

A new synthetic route to 2-substituted naphtho[2,3-b]furan-4,9-dione

Koyanagi, Jyunichi; et al, Journal of Heterocyclic Chemistry, 1997, 34(2), 407-412

Production Method 12

83-72-7

83280-65-3

Reaction Conditions

1.1 Reagents: Bromine Solvents: Pentane ;  -15 °C; 10 min, -15 °C
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.3 Solvents: Tetrahydrofuran ;  30 min, 0 °C → rt; 5 h, reflux
1.4 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ;  3 h, reflux
1.5 Reagents: Ammonium chloride Solvents: Water

Reference

In Silico and In Vitro Study of Janus Kinases Inhibitors from Naphthoquinones

Sanachai, Kamonpan ; et al, Molecules, 2023, 28(2),

Production Method 13

83-72-7

83280-65-3

Reaction Conditions

1.1 Reagents: Bromine Solvents: Pentane ;  10 min, -15 °C
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.3 Solvents: Tetrahydrofuran ;  5 h, 0 °C → reflux
1.4 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ;  reflux; 3 h, reflux
1.5 Reagents: Ammonium chloride Solvents: Water

Reference

Synthesis, biological evalution and molecular docking of avicequinone C analogues as potential steroid 5-reuctase inhibitors

Karnsomwan, Wiranpat; et al, Chemical & Pharmaceutical Bulletin, 2017, 65(3), 253-260

Production Method 14

83-72-7

83280-65-3

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  30 min, 0 °C → rt; 5 h, reflux
1.3 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ;  3 h, reflux
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

In Silico and In Vitro Study of Janus Kinases Inhibitors from Naphthoquinones

Sanachai, Kamonpan ; et al, Molecules, 2023, 28(2),

Production Method 15

171084-36-9

83280-65-3

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran

Reference

A facile synthesis of 2-acetylnaphtho[2,3-b]furan-4,9-dione

Koyanagi, Jyunichi; et al, Journal of Heterocyclic Chemistry, 1995, 32(4), 1289-91

Napabucasin Raw materials

• Iodonium, phenyl-, 3,4-dihydro-1,3,4-trioxo-2(1H)-naphthalenylide
• Ethanone, 1-(4,9-dimethoxynaphtho[2,3-b]furan-2-yl)-
• Naphtho[2,3-b]furan-4,9-dione, 2-ethyl-
• 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
• Lawsone
• 3-bromobut-3-en-2-one
• Naphtho[2,3-b]furan-4,9-dione, 2-acetyl-2,3-dihydro-2-methoxy-
• Benzoic acid, 2-[(5-acetyl-3-furanyl)carbonyl]-
• 2-acetyl-2,3,4,9-tetrahydronaphtho[2,3-b]furan-4,9-dione

Napabucasin Preparation Products

• Napabucasin (83280-65-3)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Naphthofurans Naphthofurans
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Naphthofurans

• 22985-02-0(Naphtho[2,3-b]furan-4,9-dione,3,5-dimethyl-)
• 59382-08-0(Naphtho[2,3-b]furan-4,9-dione, 3-benzoyl-2-methyl-)
• 37066-23-2(3-Furancarboxaldehyde, 2-benzoyl-)
• 38071-70-4(Ethanone, 1,1'-(5-methyl-2,4-furandiyl)bis-)
• 145663-32-7(Ethanone,1-(3-ethyl-4,5-dimethyl-2-furanyl)-)
• 62452-68-0(Naphtho[2,3-b]furan-4,9-dione, 2-butyl-)
• 5656-82-6(Naphtho[2,3-b]furan-4,9-dione)
• 915093-52-6(Naphtho[2,3-b]furan-4,9-dione, 2-ethyl-7-(4-methylpentyl)-)
• 61667-75-2(Ethanone, 1-(5-benzoyl-2-methyl-3-furanyl)-)
• 57248-30-3(Methanone, (2,5-dimethyl-3-furanyl)-2-furanyl-)