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Anticancer compound, intermediate therefor, and processes for producing these

A technology for compounds and racemates, applied in the field of anticancer compounds and their intermediates and production, can solve the problems of low yield and the like

Inactive Publication Date: 2008-03-12
TAHEEBO JAPAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, methods for obtaining 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione other than extraction from the above-mentioned plants are unknown, therefore, based on the above The scarcity of plants and their very low yield (0.05%) (for example, see: non-patent literature 1), 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-B]furan- 4,9-Diketones are not yet fully used as medicines

Method used

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  • Anticancer compound, intermediate therefor, and processes for producing these
  • Anticancer compound, intermediate therefor, and processes for producing these
  • Anticancer compound, intermediate therefor, and processes for producing these

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Preparation of 2-Dimethyljuglone

[0072]

[0073] To a solution of 5-hydroxynaphthalene-1,4-dione (also known as juglone) (171 mg, 1 mmol) in toluene (5 mL) at -20°C was added dimethylamine (0.75 mL, 2.0M solution in tetrahydrofuran, 1.5 mmol). The mixture was stirred at -20°C for 1 hour. Dimethylamine (0.75 mL, 2.0 M in tetrahydrofuran, 1.5 mmol) was then added thereto, the mixture was stirred at -20°C for 30 minutes, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform / ethyl acetate=20 / 1 (V / V)) to separate 2-dimethylaminojuglone (87.2 mg, 40%) and 3-dimethylaminojuglone (28.8 mg, 13%).

[0074] 2-Dimethylaminojuglone

[0075] Melting point: 147 to 148°C

[0076] 1 H-NMR (CDCl 3 ): δ 3.25 (s, 6H), 5.72 (s, 1H), 7.20 (dd, 1H, J = 1.2, 8.3 Hz), 7.45-7.51 (m, 2H), 13.0 (s, 1H).

[0077] 3-Dimethylaminojuglone

[0078] 1 H-NMR (CDCl 3 ): δ 3.23 (s, 6H), 5.84 (s, 1H), 7.15 (dd, 1H, J = 3.7, 6.1...

Embodiment 2

[0080] The reaction was carried out in a manner similar to that described in Example 1, except that -40°C was substituted for -20°C to obtain 2-juglone (104 mg, 48%) and 3-juglone (20 mg, 10% ).

Embodiment 3

[0082] The reaction was carried out in a manner similar to that described in Example 1, except that water was used to replace tetrahydrofuran as a solvent for dimethylamine, and 0.15 ml of aqueous dimethylamine solution (50% aqueous solution, 1.5 mmol) was used at a reaction temperature of 0 ° C to obtain 2-Dimethylaminojuglone (97 mg, 45%) and 3-Dimethylaminojuglone (67 mg, 31%). The use of water instead of organic solvents makes this method more favorable in terms of environment and safety.

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Abstract

A process for easily and inexpensively producing in high yield 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione which is a racemic modification or an optically active substance; 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione, which is useful as an intermediate for producing NFD; and an anticancer containing 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]-furan-4,9-dione as an active ingredient. 5-Hydroxynaphthalene-1,4-dione (another name: Juglone), which is available at a relatively low cost, is used as a starting material to obtain 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione through four or five steps.

Description

technical field [0001] The present invention relates to 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione and its preparation, and the preparation of 2 -(1-Hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione method. The present invention also relates to a racemate or α-isomer containing 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione as an active ingredient anticancer agent Background technique [0002] The molecular formula of 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione is: [0003] [0004] is an optically active compound contained in Bignonia, natural yew trees (Taheebo) (Tabebuia avellanedae Lorentz ex Griseb), Lorentz, Asteraceae), which has a β-isomer and is considered to have excellent Anticancer activity (for example, see: Patent Document 1). However, methods for obtaining 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione other than extraction from the above-mentioned plants are unknown, therefore, based on the above ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92A61P35/00A61K31/343
Inventor 德田春邦西村克己
Owner TAHEEBO JAPAN
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