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Compound and preparation method thereof as well as application in preparation of tumor drug resistance reversal agent

A drug resistance reversal and compound technology, which is applied in the field of medicine, can solve the problems of low yield, difficult to meet clinical application, high production cost, etc., and achieve the effect of simple reaction, drug resistance reversal and high yield

Active Publication Date: 2018-06-08
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such a yield is still low, resulting in high preparation costs, and it is difficult to meet the needs of clinical applications.

Method used

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  • Compound and preparation method thereof as well as application in preparation of tumor drug resistance reversal agent
  • Compound and preparation method thereof as well as application in preparation of tumor drug resistance reversal agent
  • Compound and preparation method thereof as well as application in preparation of tumor drug resistance reversal agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 compound (5-methoxyl-1H-indol)-3-(4-methoxyphenyl) ketone (5-Methoxy-1H-indol-3-yl) (4-methoxyphenyl)methanone ( 1c) and its synthesis

[0043]

[0044] 588mg compound of formula III, 1360mg compound of formula V, POCl of 5ml 3 ; 2 g of AlCl 3 , added in 10mL 1,2-dichloroethane, reacted at 60°C for 4h, cooled down to room temperature after the reaction, dropped into ice water, distilled with CH 2 Cl 2 The product was extracted and separated by column chromatography with a total yield of 40% and a purity of 99.5%.

[0045]IR spectrum (KBr coating cm -1 ):3151,2956,1602,1427,1026cm -1 ;

[0046] 1 H NMR spectrum (ppm): δ (ppm) 11.90 (br, 1H), 7.89 (d, J = 3.2Hz, 1H), 7.80 (d, J = 8.8Hz2H), 7.76 (d, J = 2.4Hz, 1H ),7.40(d,J=8.8Hz,1H),7.07(d,J=8.8Hz 2H),6.88(dd,J=8.8,2.4Hz,1H),3.85(s,3H),3.80(s, 3H).(solvent DMSO-d 6 , TMS internal standard)

Embodiment 2

[0047] Example 2 (4-methoxy-1H-indole)-3,5-bis(4-methoxyphenyl)methanone (4-methoxy-1H-indole-3,5-diyl)bis(( 4-methoxyphenyl)methanone)(2f) and its synthesis

[0048]

[0049] 588mg compound of formula III, 1360mg compound of formula V, POCl of 5mL 3 ; 2 g of AlCl 3 , added in 10mL 1,2-dichloroethane, reacted at 60°C for 4h, cooled down to room temperature after the reaction, dropped into ice water, distilled with CH 2 Cl 2 The product was extracted and separated by column chromatography with a total yield of 19% and a purity of 96.7%.

[0050] IR spectrum (KBr coating cm -1 ):3380,2935,1600,1361,1075cm -1 ;

[0051] 1 H NMR spectrum (ppm) 12.00 (br, 1H), 7.77 (dd, J = 8.8, 2.4Hz, 4H), 7.60-7.56 (m, 2H), 7.13 (dd, J = 8.8, 2.0Hz, 2H), 7.05(dd, J=8.8,2.0Hz,2H),6.78(d,J=8.8Hz,1H),3.89(s,3H),3.86(s,3H).(solvent DMSO-d 6 , TMS internal standard)

[0052] Drug efficacy verification

[0053] 1. Cell culture method

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Abstract

The invention relates to the technical field of medicines, in particular to a compound and a preparation method thereof as well as the application in preparation of a tumor drug resistance reversal agent. The invention provides a preparation method of a computer as shown in FORMULA II, and also provides the application of two prepared compounds in preparation of a tumor drug resistance reversal agent. According to the preparation method provided by the invention, POCl3 and AlCl3 are used as catalysts, so that only one step of reaction is needed; conditions are simple, and the yield is high. The prepared compound can reverse the drug resistance of a tumor-resistant drug, and the reversing activity of the compound is equivalent to that of an existing ABCG2 inhibitor FTC.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a compound and its preparation method and its application in the preparation of a tumor drug resistance reversal agent. Background technique [0002] Cancer, also known as malignant tumor, is a disease caused by the loss of normal regulation and excessive proliferation of body cells. Cancer is one of the diseases with the highest mortality rate. Most cancer patients will develop drug resistance after being treated with chemotherapy drugs for a period of time, resulting in poor chemotherapy effect. The mechanism of tumor multidrug resistance is complex, among which the high expression of ABC transporter in tumor cells is an important reason for tumor multidrug resistance. ABC transporters can make drugs pumped out of tumor cells, thereby reducing the anti-tumor effect of drugs. ABCG2 is one of the ABC transporters. Prior art studies have shown that one of the reasons why malign...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12A61K31/404A61P35/00
CPCC07D209/12
Inventor 汪波陈哲生蔡超云翟虹陈保利杜钊夷郭锦轩
Owner SUN YAT SEN UNIV
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