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3-substituted propyl-2-alkene-1-ketone compound and application thereof

A technology of ketone compounds and compounds, applied in the field of medicine

Inactive Publication Date: 2016-04-20
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, chalcone is a kind of 3-substituted prop-2-en-1-one compound species, and it is also a kind of natural structure existing in plants. There are literature reports on the anti-tumor effect of this type of compound, etc. effect, but it has not been reported that this type of compound has synergistic antifungal effect

Method used

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  • 3-substituted propyl-2-alkene-1-ketone compound and application thereof
  • 3-substituted propyl-2-alkene-1-ketone compound and application thereof
  • 3-substituted propyl-2-alkene-1-ketone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] The preparation of embodiment 1 (E)-1-(2-hydroxyl-6-methoxyphenyl)-3-(5-hydroxymethylfuran-2-yl) prop-2-en-1-one (1 )

[0107]

[0108] Take 500mg (3.0mmol) of 2-hydroxy-6-methoxyacetophenone and 600mg (3.6mmol) of 5-hydroxymethylfurfural and add it to 15ml ethanol, then add 30% NaOH aqueous solution, and stir the reaction at room temperature After 24-48 hours, TLC showed that the reaction was almost complete. The reaction liquid was poured into ice water, filtered, and the solid was washed with water three times. After drying, it was separated by flash column to obtain compound (1), 312 mg, with a yield of 38%.

[0109] 1 H-NMR: 3.95 (3H, s, -OCH3), 4.69 (2H, s, -CH 2 -); 6.43(2H,m,Ar-H); 6.60(1H,dd,J 1 =8.4Hz,J 2 = 0.9Hz, Ar-H); 6.66 (1H, d, J = 3.3Hz, Ar-H); 7.38 (2H, m, Ar-H); 7.57 (1H, d, J = 15.3Hz, α-H ); 7.74 (1H, d, J = 15.3 Hz, β-H); 13.18 (1H, s, -OH). m + = 275.2.

Embodiment 2

[0110] The preparation of embodiment 2 (E)-1-(2-hydroxyl-4-methoxyphenyl)-3-phenylprop-2-en-1-one (2)

[0111]

[0112] Using 2-hydroxy-4-methoxyacetophenone and benzaldehyde as raw materials, refer to the synthesis method of compound 1.

[0113] 1 H-NMR: 3.87(3H,s,-OCH 3 ),6.49(1H,s),6.52(1H,d,J=2.4,Ar-H),7.43(3H,m,Ar-H),7.67(1H,d,J=15.3Hz,Ar-H) ,7.65(2H,m,Ar-H),7.84(1H,d,J=9.3Hz),7.90(1H,d,J=15.3Hz),13.43(1H,s,-OH).M + = 255.2.

Embodiment 3

[0114] The preparation of embodiment 3 (E)-1-(2-hydroxyl-6-methoxyphenyl)-3-(thien-2-yl) prop-2-en-1-one (3)

[0115]

[0116] Using 2-hydroxy-6-methoxyacetophenone and thiophenecarbaldehyde as raw materials, refer to the synthesis method of compound 1.

[0117] 1 H-NMR: 3.07(3H,s,-OCH 3 ),6.43(1H,dd,J 1 =1.2,J 2 =8.4,Ar-H),6.61(1H,dd,J 1 =0.9,J 2 =8.1,Ar-H),7.10(1H,m,Ar-H),7.35(2H,m,Ar-H),7.41(1H,m,Ar-H),7.71(1H,d,J=15.3 ), 7.75 (1H, d, J = 15.3), 13.18 (1H, s, -OH). m + = 261.2.

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Abstract

The invention relates to the technical field of medicine and particularly discloses a 3-substituted propyl-2-alkene-1-ketone compound and application thereof to preparation of antifungal drugs and synergistic antifungal drugs. The compound can be used together with azole type antifungal drugs and improve sensibility of drug-resistance bacteria to the azole type antifungal drugs, so that the reversing drug-resistance effect is achieved, and the synergistic antifungal effect is generated.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the application of a 3-substituted prop-2-en-1-one compound and its cooperation with fluconazole in the preparation of an antitumor drug composition. Background technique [0002] Mycoses are diseases caused by fungi. As a class of eukaryotic organisms that widely exist in nature, fungi can infect different parts of the human body. From the perspective of clinical pathogenicity, mycoses can be divided into two categories: superficial mycosis and deep mycosis. Many problems, such as the abuse of antibiotics, lead to the destruction of the normal flora symbiotic relationship between bacteria and fungi; secondly, in clinical application, more and more organ transplantation operations are carried out in clinical practice, and the use of immunosuppressants after surgery has affected the The normal immune function of the body reduces the body's resistance to fungi. The above problem...

Claims

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Application Information

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IPC IPC(8): C07D307/46C07C49/84C07D333/22C07C49/835C07D317/54C07C225/22C07D213/50A61K31/341A61K31/12A61K31/381A61K31/36A61K31/136A61K31/4406A61P31/10
CPCC07C49/835C07C49/84C07C225/22C07D213/50C07D307/46C07D317/54C07D333/22
Inventor 金永生刘守炜董怀怀刘思宇王元花赵菲姜远英
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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