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Benzoxazole ketones derivative and preparation method thereof

A technology for benzoxazolones and derivatives, applied in the field of novel compounds and their preparation, can solve problems such as no 4-position substituted derivatives, achieve suitable large-scale industrial production, simple operation, and single reaction results. Effect

Inactive Publication Date: 2008-10-29
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The present invention provides a kind of benzoxazolone derivative and its preparation method

Method used

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  • Benzoxazole ketones derivative and preparation method thereof
  • Benzoxazole ketones derivative and preparation method thereof
  • Benzoxazole ketones derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 4-hydroxy-benzoxazolone IV.

[0031] 2-Amino-resorcinol was placed in a 250mL round-bottomed flask, and 100mL of tetrahydrofuran solution was added dropwise, then a tetrahydrofuran solution of triphosgene (BTC), and 2-amino-resorcinol and triphosgene were added dropwise. The molar ratio is 1:1.2~2.0, the reaction solution is brown, refluxed for 2~5h under the protection of nitrogen, the reflux temperature is 55~75°C, column chromatography (6%CH 3 OH / CH 2 Cl 2 Elution), a brownish-yellow solid was obtained with a yield of 78.8%. 1 H NMR (600MHz, CD 3 OD): δ6.643(d, J=7.959Hz, 1H, ArH), 6.737(d, J=7.959Hz, 1H, ArH), 6.879(t, J=8.223Hz, 1H, ArH), 10.127(s , 1H, OH), 11.540 (d, 1H, NH). ESI-MS m / z: 150.23 ([M-H] - ).

Embodiment 2

[0032] Example 2: Preparation I-1 of 4-benzoyloxy-benzoxazolone

[0033] Weigh 100mg (0.66mmol) of 4-hydroxy-benzoxazolone IV into a round bottom flask, add anhydrous acetonitrile to dissolve, then add 35mg (0.99mmol) of ammonia water, add dropwise 139mg (0.99mmol) of benzoyl chloride under ice cooling mmol) in acetone solution, continue to react until the white mist disappears, then react at room temperature for 30min, and reflux at 80°C for 6h. The molar ratio of the above-mentioned compound IV to compound benzoyl chloride and phosphonic acid agent is 1: 1.5: 1.5. Separation by silica gel column chromatography (20% ethyl acetate / petroleum ether) gave 47 mg of white solid powder, yield 27.9%, mp 202.2-202.5°C. 1 H NMR (300MHz, CDCl 3 )δ7.160(m, 3H, ArH), 7.590(t, J=7.336Hz, 2H, ArH), 7.727(t, J=7.336Hz, 1H, ArH), 8.262(d, J=7.336Hz, 2H , ArH), 8.50 (s, 1H, NH). ESI-MS m / z: 256 ([M+H] + ).

Embodiment 3

[0034] Example 3: Preparation I-1 of 4-benzenesulfonyloxy-benzoxazolone

[0035] Weigh 100 mg (0.66 mmol) of 4-hydroxy-benzoxazolone and place it in a round-bottomed flask, add anhydrous tetrahydrofuran to dissolve it, then add 48 mg (0.66 mmol) of diethylamine, and add dropwise 117 mg of benzenesulfonyl chloride ( 0.66mmol) of acetone solution, continue to react until the white mist disappears, then react at room temperature for 30min, and reflux at 60°C for 4h. The molar ratio of the above-mentioned compound IV to compound benzoyl chloride and formic acid agent is 1:1.0:1.0. After separation by silica gel column chromatography (20% ethyl acetate / petroleum ether), 79 mg of white solid powder was obtained, with a yield of 41.1%, and mp 181-185°C. 1 H NMR (600MHz, CDCl 3 )δ6.557(d, J=8.597Hz, 1H, ArH), 6.946(t, J=8.309Hz, 1H, ArH), 7.102(d, J=8.309Hz, 1H, ArH), 7.580(t, J =7.743Hz, 2H, ArH), 7.734(t, J=7.527Hz, 1H, ArH), 7.873(d, J=7.554Hz, 2H, ArH), 8.067(s, 1H, NH). ESI-MS...

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Abstract

The invention relates to a series of novel compounds and a preparation method thereof, particularly to a series of benzoxazolone derivatives and a preparation method thereof, and solves the problem that the prior benzoxazolone compounds have no 4-substituted derivatives and have anti-HBV activity and anti-HIV activity. The general structural formula of the derivatives is shown in the figure, wherein R is C3-C6 fatty acid ester group, benzoate group / substituted benzoate group, benzene sulfonate group / substituted benzene sulfonate group, amino acid ester group, or heterocyclic acid ester group / substituted heterocyclic acid ester group. The invention obtains a series of 4-substituted benzoxazolone derivatives with proven anti-HBV activity and anti-HIV activity, opens new preparation paths of the above three drugs, and brings new breakthrough in pharmaceutical and pesticide fields. In addition, the synthetic method has the advantages of easy operation, mild reaction conditions, single reaction product, and applicability to large scale production.

Description

technical field [0001] The invention relates to a class of novel compounds and a preparation method thereof, in particular to benzoxazolone derivatives and a preparation method thereof. Background technique [0002] Benzoxazolone compounds are unique chemical components present in plants such as Poaceae, Acanthaceae, Ranunculaceae, Scrophulariaceae, etc. They play a defensive role against bacteria, fungi, insects, etc., and are often used as organic dyes , pigments, pesticides, etc. [0003] Due to the unique antibacterial and antiviral activity of the parent structure of benzoxazolone, many derivatives of benzoxazolone have been developed, such as chlorzoxazone (5-chloro-benzoxazolone), 6-chloro- Benzoxazolone, etc., the structural formula is shown in the figure: [0004] [0005] Benzoxazolone Benzoxazolone Derivatives [0006] A large number of literature reports at home and abroad show that benzoxazolone compounds have anti-inflammatory and antibacterial activities...

Claims

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Application Information

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IPC IPC(8): C07D263/58C07D413/12A61K31/421A61K31/4439A61P1/16A61P31/12A61P31/18A61P29/00
Inventor 李青山唐莉班树荣冯秀娥
Owner SHANXI MEDICAL UNIV
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