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2-alkoxy chromone oxime derivative and preparation method and application thereof

A technology for alkoxychromone oxime and derivatives, which is applied in the field of preparation of organic compounds, can solve problems such as high requirements for reaction conditions, and achieve the effects of obvious bacteriostatic effect, obvious tumor cell proliferation inhibition effect, and high yield.

Active Publication Date: 2017-02-15
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, in the process of preparing oxime derivatives in the prior art, metal catalysts are used, and the reaction conditions are very demanding; therefore, new methods need to be developed to prepare various oxime derivatives at low cost and under mild conditions, so as to expand wider applications

Method used

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  • 2-alkoxy chromone oxime derivative and preparation method and application thereof
  • 2-alkoxy chromone oxime derivative and preparation method and application thereof
  • 2-alkoxy chromone oxime derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 2-methoxychroman-4-one-3-oxime

[0033] With 4-oxo-4H-benzopyran-3-carbaldehyde and sodium nitrite as raw materials, the reaction steps are as follows:

[0034] Add 4-oxo-4H-chromene-3-carbaldehyde (0.174 g, 1.0 mmol), sodium nitrite (0.069 g, 1.0 mmol), di-tert-butyl peroxide (0.584 g, 4.0 mmol), methanol (2 ml) and acetonitrile at room temperature;

[0035] TLC tracking reaction until complete completion;

[0036] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (yield 70%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 13.55 (s, 1H), 7.90 (dd, J = 7.8, 1.4 Hz, 1H), 7.76 – 7.59 (m, 1H), 7.31 – 7.06 (m, 2H), 6.39 (s,1H), 3.51 (s, 3H).

Embodiment 2

[0037] Example 2: Synthesis of 2-methoxy-6-fluorochroman-4-one-3-oxime

[0038] Using 6-fluoro-4-oxo-4H-benzopyran-3-carbaldehyde and sodium nitrite as raw materials, the reaction steps are as follows:

[0039] Add 6-fluoro-4-oxo-4H-chromene-3-carbaldehyde (0.192 g, 1.0 mmol), sodium nitrite (0.138 g, 2.0 mmol), tert-butyl peroxybenzoate to the reaction flask (0.776 g, 4.0 mmol), methanol (2 ml) and 1,2-dichloroethane at room temperature;

[0040] TLC tracking reaction until complete completion;

[0041] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (yield 90%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO-d 6 ): δ 13.70 (s, 1H), 8.13 – 7.36 (m, 2H), 7.43 – 6.97 (m, 1H), 6.34 (s, 1H), 3.48 (s, 3H).

Embodiment 3

[0042] Example 3: Synthesis of 2-methoxy-6-chlorochroman-4-one-3-oxime

[0043] Using 6-chloro-4-oxo-4H-benzopyran-3-carbaldehyde and sodium nitrite as raw materials, the reaction steps are as follows:

[0044] Add 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (0.209 g, 1.0 mmol), sodium nitrite (0.207 g, 3.0 mmol), dicumyl peroxide ( 1.080 g, 4.0 mmol), methanol (2 mL) and acetone at room temperature;

[0045] TLC tracking reaction until complete completion;

[0046] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (yield 86%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 13.76(s, 1H), 7.81(d, J = 2.7 Hz, 1H), 7.73 (dd, J = 8.8, 2.7 Hz, 1H), 7.25 (d, J = 8.8 Hz,1H), 6.40 (s, 1H), 3.51 (s, 3H).

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Abstract

The invention discloses a 2-alkoxy chromone oxime derivative and a preparation method and application thereof. The preparation method includes: dissolving a 3-formyl chromone derivative, sodium nitrite, an alcohol derivative and an oxidizing agent into a solvent, and performing reaction under room temperature to obtain the 2-alcoxyl chromone oxime derivative. The preparation method has the advantages that the 3-formyl chromone derivative used as the initiator is easy to obtain, low in cost and many in variety; the sodium nitrite used as the oximation reagent is low in cost; metal catalysts are not needed, metal residues can be avoided, and the method is suitable for preparing medicine and biological preparations; the reaction of the method is performed in the air, and the method is mild in reaction condition, short in reaction time, high in target product yield, simple in reaction operation and post-treatment, low in environment pollution and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of 2-alkoxychromone oxime derivatives; the invention also relates to the use of such compounds in the preparation of tumor cell proliferation inhibitors and antibacterial agents. Background technique [0002] Oximes are an important class of organic compounds, widely used in the fields of synthetic chemistry, coordination chemistry and biomedicine. Oxime derivatives have a wide range of physiological activities, such as antioxidant, antibacterial, insecticidal and other activities. [0003] Linwood K. Payne, Jr. et al. reported that oxime derivatives have insecticidal activity, and the structures of their representative compounds are as follows (see: Payne, Linwood K., Jr.; Stansbury, Harry A., Jr.; Weiden, M. H.J. J. Agric. Food. Chem. 1966, 14(4) , 356.): [0004] [0005] Filip Jaroš et al. reported that oxime der...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/56A61K31/352A61P35/00A61P31/04
CPCC07D311/56
Inventor 邹建平周鹏骏张沛之孙网彬
Owner SUZHOU UNIV
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