7-substituted-4-aryl coumarins compound, and preparation method and application thereof

A technology for aryl coumarins and compounds, applied in the field of 7-substituted-4-aryl coumarins and their preparation, can solve the problems of poor drug selectivity, toxic and side effects, etc., and achieve mild reaction conditions and cheap reagents , The effect of easy synthesis method

Active Publication Date: 2017-05-17
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional drugs have poor selectivity, and they can also kill normal tissue cells while killing tumor cells, resulting in obvious toxic side effects

Method used

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  • 7-substituted-4-aryl coumarins compound, and preparation method and application thereof
  • 7-substituted-4-aryl coumarins compound, and preparation method and application thereof
  • 7-substituted-4-aryl coumarins compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 N-[2-(8-methyl-2-carbonyl-4-phenyl-2H-benzopyran-7-oxygen)acetyl]-L-prolineamide (T 1 ) preparation

[0039] Synthetic route such as figure 1 Shown:

[0040] (1) Synthesis of ethyl benzoyl acetate (beta ketoester)

[0041] Weigh benzoic acid, add it to dissolve in absolute ethanol, slowly add concentrated H 2 SO 4 , stop the reaction after heating to reflux for 16h, remove ethanol by rotary evaporation, and use saturated Na 2 CO 3 Adjust the pH to 8-9, extract 3 times with ethyl acetate, combine the organic phases, anhydrous Na 2 SO 4 After drying, the ethyl acetate was removed by rotary evaporation to obtain a colorless oily liquid (ethyl benzoate), which was directly used in the next reaction.

[0042] Weigh ethyl benzoate, add NaOEt and ethyl acetate, heat to reflux for 10h, stop the reaction, remove ethyl acetate by rotary evaporation, adjust pH to 8-9 with 2mol / L HCl, extract 3 times with ethyl acetate, combine Organic phase, anhydrous Na 2 SO ...

Embodiment 2

[0052] Example 2 2-(8-Methyl-2-carbonyl-4-phenyl-2H-benzopyran-7-oxygen)acetamide (T 2 ) preparation

[0053] The preparation method is the same as in Example 1, replacing L-prolinamide with ammonium chloride. Yield: 51.28%, mp: 268-271°C.

[0054] 1 H-NMR (400MHz, DMSO-d 6 ): δ7.57-7.58(t, 3H, Ar-H), 7.46-7.53(m, 4H, Ar-H), 7.23-7.26(d, 1H, J=8.8Hz, -CON H 2 ), 6.91-6.93 (d, 1H, J=8.8Hz, -CON H 2 ), 6.26(s, 1H, Ar-H), 4.60(s, 2H, -CO-CH 2 -O-), 2.32(s, 3H, Ar-CH 3 )ppm. EI-MS (m / z): 309 (M + ).

Embodiment 3

[0055] Example 3 N-(2-(dimethylamino)ethyl)-2-(8-methyl-2-carbonyl-4-phenyl-2H-benzopyran-7-oxygen)acetamide (T 3 ) preparation

[0056] The preparation method is the same as in Example 1, except that L-prolineamide is replaced by N,N-dimethyl-1,2-ethylenediamine. Yield: 61.22%, mp: 238-241°C.

[0057] 1H-NMR (400MHz, DMSO-d 6 ): δ7.92-7.94 (t, 1H, -CH 2 CON H -), 7.56-7.58 (t, 3H, Ar-H), 7.50-7.52 (q, 2H, Ar-H), 7.22-7.24 (d, 1H, J=8.8Hz, 5'Ar-H), 6.93 -6.95(d, 1H, J=9.2Hz, 6'Ar-H), 6.26(s, 1H, 3'Ar-H), 4.64(s, 2H, -CO-CH 2 -O-), 3.22-3.25(t, 2H, -NHC H 2 CH 2 N(CH 3 ) 2 ), 2.30-2.33 (t, 5H, -NHCH 2 C H 2 N(CH 3 ) 2 and Ar-CH 3 ), 2.15(s, 6H, -NHCH 2 CH 2 N(C H 3 ) 2 )ppm. ESI-MS(m / z): 381.2[M+H] + .

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PUM

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Abstract

The invention discloses a 7-substituted-4-aryl coumarins compound, and a preparation method and an application thereof and belongs to the technical field of antitumor drugs. The 7-substituted-4-aryl coumarins compound is acquired in the manner of modifying and remolding 4 and 7 loci of the coumarins. The structural formula is shown in the specification. A pharmacological experiment proves that such a compound has an excellent antitumor activity, can be used for preparing the antitumor drugs, is capable of supplying a new selection for the development and application of the antitumor drugs and further can be applied to the design and optimization of the antitumor drugs. The preparation method of the compound has the advantages of easily acquired raw materials, mild reaction condition, easily realized synthesis method, simple reaction process and operation, low-cost reagents and higher yield.

Description

technical field [0001] The invention belongs to the technical field of antineoplastic drugs, relates to a 7-substituted-4-aryl coumarin compound and its preparation method and application, and provides a new choice for the development and application of antineoplastic drugs. Background technique [0002] Malignant tumors are one of the diseases that seriously threaten human health. According to the results of national tumor registration in 2013, the incidence of malignant tumors in China is 235 / 100,000. Lung cancer and breast cancer rank first in males and females respectively. The incidence of malignant tumors in China has been on the rise in the past ten years, and the incidence is close to the world level. However, the mortality rate of malignant tumors is higher than the world level. In 2012, the number of malignant tumors in China was 3.065 million, accounting for about one-fifth of the global incidence; the number of malignant tumor deaths was 2.205 million, accounting...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C07D405/12A61K31/4025A61K31/37A61K31/5377A61K31/496A61P35/00
CPCC07D311/16C07D405/12
Inventor 李义平赵阳高艳娟马影金政宇胡延祯王亚文
Owner XI AN JIAOTONG UNIV
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