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Benzyl cyclohexenone derivative and preparation method and medical application thereof

A technology of cyclohexenone and benzylidene, applied in the preparation of carbon-based compounds, the preparation of cyanide reactions, the preparation of organic compounds, etc.

Active Publication Date: 2017-05-17
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The designed compound not only optimizes the PL structure, simplifies the synthetic route, but also improves the inhibitory rate of the inventive compound on sensitive tumor cells and drug-resistant tumor cells. Through in-depth research on the drug action mechanism and biological characteristics of this type of compound, the present invention discloses A class of novel benzylidene cyclohexenone derivatives and their pharmaceutically acceptable salts that can promote the ROS level of tumor cells, there is no report on this type of compounds

Method used

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  • Benzyl cyclohexenone derivative and preparation method and medical application thereof
  • Benzyl cyclohexenone derivative and preparation method and medical application thereof
  • Benzyl cyclohexenone derivative and preparation method and medical application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0078] Embodiment 1 (E)-6-(4-methoxyphenylvinylidene) cyclohexen-2-ketone (I 1 )

[0079] Dissolve the raw material cyclohexen-2-one (0.95g, 10.0mmol) in 15ml of anhydrous dichloromethane, and then add 200mg of TiCl at -50°C 4 and PPh 3 (2.62g, 10.0mmol), 4-methoxybenzaldehyde (2.72g, 20.0mmol) was added after 15min, and reacted overnight at room temperature. Add 10% K after the reaction is complete 2 CO 3 The solution was treated for 10 min, the organic layer was collected, rotary evaporated, and purified by column chromatography. 1.69 g of solid were obtained, yield: 79%. 1 H NMR (DMSO-d 6 ,300MHz): δ7.54(s,1H,ArCH=C),7.31(d,2H,J=0.60Hz Ar-H),6.97(dt,1H,CH=C H CO),6.89(m,1H,Ar-H),6.18(dt,1H,C H =CHCO),3.80(s,3H,OCH 3 ),2.99(m,2H,CH 2 ),2.38(m,2H,CH 2 ).MS(ESI)m / z:215[M+H] + .

Embodiment 2

[0080] Embodiment 2 (E)-6-(3-methoxyphenylvinylidene) cyclohexen-2-ketone (I 2 )

[0081] Dissolve the raw material cyclohexen-2-one (0.95g, 10.0mmol) in 15ml of anhydrous dichloromethane, and then add 200mg of TiCl at -50°C 4 and PPh 3 (2.62g, 10.0mmol), 3-methoxybenzaldehyde (2.72g, 20.0mmol) was added after 15min, and reacted overnight at room temperature. Add 10% K after the reaction is complete 2 CO 3 The solution was treated for 10 min, the organic layer was collected, rotary evaporated, and purified by column chromatography. 1.71 g of solid were obtained, yield: 80%. 1 H NMR (DMSO-d 6 ,300MHz):δ7.54(s,1H,ArCH=C),7.27(m,1H,Ar-H),7.00(m,1H,Ar-H),6.93(d,1H,CH=C H CO),6.84(m,1H,Ar-H),6.20(m,1H,C H =CHCO),3.79(s,3H,OCH 3 ),2.99(m,2H,CH 2 ),2.39(m,2H,CH 2 ).MS(ESI)m / z:215[M+H] + .

Embodiment 3

[0082] Example 3 (E)-6-(4-(trifluoromethoxy) phenylvinylidene) cyclohexen-2-one (I 3 )

[0083] Dissolve the raw material cyclohexen-2-one (0.95g, 10.0mmol) in 15ml of anhydrous dichloromethane, and then add 200mg of TiCl at -50°C 4 and PPh 3 (2.62g, 10.0mmol), 4-trifluoromethoxybenzaldehyde (3.80g, 20.0mmol) was added after 15min, and reacted overnight at room temperature. Add 10% K after the reaction is complete 2 CO 3 The solution was treated for 10 min, the organic layer was collected, rotary evaporated, and purified by column chromatography. 2.25 g of solid were obtained, yield: 84%. 1 H NMR (DMSO-d 6 ,300MHz):δ7.49(s,1H,ArCH=C),7.32(m,2H,Ar-H),7.17(m,2H,Ar-H),6.98(dt,1H,CH=C H CO),6.17(dt,1H,C H =CHCO),2.92(m,2H,CH 2 ),2.36(m,2H,CH 2 ).MS(ESI)m / z:269[M+H] + .

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Abstract

The invention discloses a benzyl cyclohexenone derivative and a preparation method and medical application thereof. The benzyl cyclohexenone derivative is a compound in a general formula I. The compound can be individually prepared into a preparation or can be combined with one or more pharmaceutically acceptable carriers to prepare the preparation for administration. The compound can be combined with other antitumor drugs for application, and can also be combined with radiotherapies for application. These antitumor drugs or radiotherapies and the compound disclosed by the invention can be given at the same time or different times. These combination therapies can generate a synergistic effect to improve the treatment effect.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to a class of benzylidene cyclohexenone derivatives and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions containing these derivatives and their medical applications, especially Application in preparing drugs for malignant tumors and anti-drug-resistant malignant tumors. Background technique [0002] Cancer is the second leading cause of death in humans after cardiovascular disease. Although a variety of anti-tumor drugs are available clinically, due to the complexity of tumor etiology, drug resistance of tumors, and toxic and side effects of anti-tumor drugs, the existing drugs still cannot meet the needs of treatment. Therefore, it is of great significance to find new anti-tumor drugs with high efficacy, strong targeting and less side effects. [0003] [0004] A large number of studies have shown that finding new drugs from natu...

Claims

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Application Information

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IPC IPC(8): C07C49/753C07D317/54C07C205/45C07D213/50C07D333/22C07D307/46C07D215/14C07D277/64C07D209/12C07D209/86C07C255/46C07C253/14C07C201/12C07C45/63A61K31/122A61K31/277A61K31/36A61K31/4406A61K31/341A61K31/381A61K31/403A61K31/404A61K31/428A61P35/00
CPCC07C49/753C07C205/45C07C255/46C07D209/12C07D209/86C07D213/50C07D215/14C07D277/64C07D307/46C07D317/54C07D333/22
Inventor 凌勇苏星彭炎福郭靖朱鹏刘季李洋阳朱睿杨秋星王婷婷
Owner NANTONG UNIVERSITY
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