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Formononetin derivatives containing carbadithiocarbamate, preparation method and application in antitumor drugs

A technology containing aminodithiocarbamate and formononetin, applied in antitumor drugs, drug combinations, organic chemistry, etc., can solve the problem of weak antitumor activity, improve antitumor activity, and solve the Weak tumor activity, the effect of broadening the research field

Inactive Publication Date: 2018-09-04
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a series of novel formononetin derivatives containing carbamodithioformate to solve the problem of weak antitumor activity of the natural product formononetin

Method used

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  • Formononetin derivatives containing carbadithiocarbamate, preparation method and application in antitumor drugs
  • Formononetin derivatives containing carbadithiocarbamate, preparation method and application in antitumor drugs
  • Formononetin derivatives containing carbadithiocarbamate, preparation method and application in antitumor drugs

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Experimental program
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Effect test

Embodiment 1

[0027] Example 1 Preparation of general formula (1a~1d)

[0028] In 100ml tetrahydrofuran, react 10g formononetin, 6.2g potassium carbonate and 7g 1,2-dibromoethane or 7.5g 1,3-dibromopropane or 8g 1,4-dibromobutane at 80°C Heat and stir. After 6 hours of reaction, the system was concentrated to dryness, and 10 ml of ethanol was added for recrystallization to obtain compounds 1a to 1d.

Embodiment 2

[0029] The preparation of embodiment 2 general formula (I1~I9)

[0030] In 10ml of acetone, 1g of compound (1a~1d) was reacted with 600mg of substituted secondary amine, 300mg of carbon disulfide, and 440mg of sodium phosphate at room temperature. After the reaction was completed, suction filtration, the filtrate was concentrated, and 3ml of ethanol was recrystallized to obtain the general formula (I1~ I9) Compounds.

[0031] The general formula (I1~I9) structure is characterized as follows:

[0032] I-1: Yield 83%. White solid. Mp: 124~125℃. 1 H NMR (400MHz, DMSO) δ 8.42(s, 1H), 8.03(d, J=8.9Hz, 1H), 7.53(d, J=8.7Hz, 2H), 7.38–7.29(m, 4H), 7.29 –7.22(m,1H),7.17(d,J=2.2Hz,1H),7.09(dd,J=8.9,2.3Hz,1H),7.00(d,J=8.8Hz,2H),4.22(t, J=6.1Hz, 4H), 3.92(s, 2H), 3.79(s, 3H), 3.51(s, 2H), 3.42(t, J=7.2Hz, 2H), 2.45(s, 4H), 2.22– 2.09(m,2H). 13 C NMR(100MHz,DMSO)δ194.74,174.60,162.81,158.99,157.38,153.45,137.53,130.04,128.91,128.22,127.09,126.96,124.05,123.35,117.63,115.02,113.60,101...

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Abstract

The invention discloses a formononetin derivative comprising dithiocarbamate, and a preparation method and application of the formononetin derivative to antitumor drugs, and belongs to the field of pharmaceutical chemistry. The mother nucleus of formononetin is combined with a dithiocarbamate active unit to simply, efficiently and greenly synthesize the formononetin derivative comprising dithiocarbamate. The general molecular formula of the formononetin derivative comprising dithiocarbamate is shown in the description. The in vitro antitumor activity test of the compound indicates that the formononetin derivative has a certain effect of inhibiting multiple tumor cells of EC-109, MGC-803 and PC-3. Compared with the natural formononetin, the anti-prostate cancer activity of the formononetin derivative I-8 comprising dithiocarbamate is improved by 28 times, so that the formononetin derivative comprising dithiocarbamate is a candidate or a lead compound for further development, and is applied to the preparation of the antitumor drugs.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a new class of aminodithiocarboxylate-containing formononetin derivatives, their preparation method and their application as a new class of antitumor drug lead compounds. Background technique [0002] Formononetin It is the inflorescence and flowered branches and leaves of the natural plant red clover. It belongs to isoflavones and has a certain effect on the prevention of breast cancer, prostate cancer and other cancers. The anti-tumor mechanism indicated that the natural product formononetin induces the cycle arrest of breast cancer cells through the IGF1 / PI3K / Akt pathway and can be used as a candidate anti-tumor drug. However, the main defect of formononetin as a candidate antitumor drug is its weak activity, which is greatly limited in the application process. For example, the group of Xin Chen reported the antiproliferative activity of formononetin in vitro, and its act...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/36A61P35/00
CPCC07D311/36
Inventor 张雁冰付冬君毛若望宋健赵若含张赛扬赵兵刘英超刘宏民
Owner ZHENGZHOU UNIV
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