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Formononetin derivative comprising dithiocarbamate, preparation method and application thereof to antitumor drugs

A technology containing carbamodithiocarbamate and formononetin, which is applied in the fields of antineoplastic drugs, drug combinations, organic chemistry, etc., can solve the problems of weak antitumor activity, improve antitumor activity, and solve the problem of antitumor activity. The effect of weak tumor activity and widening the field of research

Inactive Publication Date: 2017-05-17
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 derivative comprising dithiocarbamate, preparation method and application thereof to antitumor drugs
  • Formononetin derivative comprising dithiocarbamate, preparation method and application thereof to antitumor drugs
  • Formononetin derivative comprising dithiocarbamate, preparation method and application thereof to antitumor drugs

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Embodiment 1

[0027] The preparation of embodiment 1 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 reacting for 6 hours, the system was concentrated to dryness, and 10 ml of ethanol was added for recrystallization to obtain compounds 1a-1d.

Embodiment 2

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

[0030] In 10ml of acetone, react 1g of compound (1a~1d) with 600mg of substituted secondary amine, 300mg of carbon disulfide, and 440mg of sodium phosphate at room temperature. After the reaction is completed, filter with suction, concentrate the filtrate, and recrystallize from 3ml of ethanol 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) δ8.42 (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)δ194.74,174.60,162.81,158.99,157.38,153.45,137.53,130.04,128.91,128.22,127.09,126.96,124.05,123.35,117.63,115.02,113.60,101.12,...

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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 class of novel formononetin derivatives containing carbamodithioate, their preparation method and their application as a class of new antitumor drug lead compounds. Background technique [0002] Formononetin It is the inflorescence and flowering branches and leaves of the natural plant red clover, which belongs to isoflavone compounds and has a certain effect on preventing breast cancer, prostate cancer and other cancers. The anti-tumor mechanism shows that the natural product formononetin induces cycle arrest of breast cancer cells through the IGF1 / PI3K / Akt pathway, which 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 restricted in the application process. For example, the Xin Chen group reported the in vitro antiproliferative activity of formononetin, and its activi...

Claims

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Application Information

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Patent Type & Authority Applications(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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