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7,4'-disubstituted isoflavone derivative and preparation method and application thereof

One – the technology of dihydroxy isoflavones and isoflavones, applied in the field of medicinal chemistry, can solve the problems of insignificant improvement of anti-tumor activity and poorly developed anti-tumor activity of isoflavones

Inactive Publication Date: 2014-12-31
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The antitumor activity data of the compounds involved in the existing structure-activity relationship research shows that the antitumor activity of most synthetic derivatives is not significantly improved compared with isoflavones themselves, so it can be seen that the antitumor activity of isoflavones has not been greatly improved. good development

Method used

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  • 7,4'-disubstituted isoflavone derivative and preparation method and application thereof
  • 7,4'-disubstituted isoflavone derivative and preparation method and application thereof
  • 7,4'-disubstituted isoflavone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Synthesis of 7,4'-two (2,3-epoxypropoxyl) isoflavones

[0022] Dissolve 7,4'-dihydroxyisoflavone (10g, 0.0394mol) in 150ml DMSO, add NaOH (3.2g, 0.08mol) and epichlorohydrin (16ml, 0.2mol), and react at 70°C overnight to saturate saline and CH 2 Cl 2 Extraction, and column chromatography to separate the crude product to obtain 7,4'-bis(2,3-epoxypropoxy)isoflavone. Pale yellow solid, yield 55%. 1 H NMR (400MHz, CDCl 3 )δ8.15(d,J=8.9Hz,1H),7.85(s,1H),7.42(t,J=5.8Hz,2H),6.95(dd,J=9.0,2.4Hz,1H),6.92( d,J=8.8Hz,2H),6.82(d,J=2.3Hz,1H),4.33–4.16(m,2H),3.94(td,J=11.1,5.8Hz,2H),3.37–3.28(m ,2H),2.87(dt,J=15.0,4.5Hz,2H),2.72(ddd,J=10.6,4.8,2.6Hz,2H). 13 C NMR (101MHz, CDCl 3 )δ175.78,162.70,158.49,157.79,152.21,130.19,127.97,124.82,124.75,118.79,114.73,114.68,101.06,69.31,68.81,50.15,49.79,458.76,44 21 h 18 o 6 :C68.85,H4.95;Found C68.81,H4.96.

Embodiment 2

[0023] Example 2: Synthesis of 7,4'-bis(2-hydroxyl-3-aminopropoxy)isoflavones

[0024] 7,4'-bis(2,3-epoxypropoxy)isoflavone (0.4g, 0.00109mol) was dissolved in 50mlCHCl 3 , add potassium carbonate (0.5g, 0.0036mol) and secondary amine (0.01mol), react at 70 ° C for 24 hours, with saturated saline and CH 2 Cl 2 Extraction and column chromatography to separate the crude product to obtain 7,4'-bis(2-hydroxy-3-aminopropoxy)isoflavone.

[0025] 7,4'-bis(2-hydroxy-3-di-n-aminopropoxy)isoflavone (2b). Pale yellow oily liquid, yield 65%. 1 H NMR (400MHz, CDCl 3 )δ:8.20(d,J=8.9Hz,1H),7.92(s,1H),7.49(d,J=8.7Hz,2H),7.07–6.96(m,3H),6.89(d,J=2.3 Hz,1H),4.10–3.97(m,6H),2.64–2.40(m,12H),1.59–1.41(m,8H),0.90(td,J=7.3,2.5Hz,12H). 13 C NMR (101MHz, CDCl 3 )δ:175.86,163.18,158.86,157.84,152.13,130.10,127.78,124.84,124.43,118.55,114.84,114.60,100.82,71.02,70.55,65.92,65.70,57.23,56.93,56.25,56.22,20.30,20.29,11.80 .Anal.Calcd.for C 33 h 48 N 2 o 6 :C69.69,H8.51N4.93;Found C69.65,H8.52...

Embodiment 3

[0027] Example 3: Synthesis of 7,4'-bis(3-bromopropoxy)isoflavones

[0028] Dissolve 7,4'-dihydroxyisoflavone (5g, 0.0197mol) in 100ml DMSO, add NaOH (1.6g, 0.04mol) and 1,3-dibromopropane (10ml, 0.1mol), and react at 70°C overnight. The reaction system was poured into 1M NaOH aqueous solution, the precipitate was collected, washed and dried, and the crude product was separated by column chromatography to obtain 7,4'-bis(3-bromopropoxy)isoflavone. Pale yellow solid, yield 70%. 138-141°C. 1 H NMR (400MHz, CDCl 3 )δ:8.22(d,J=8.9Hz,1H),7.92(d,J=2.8Hz,1H),7.53–7.46(m,2H),7.02–6.95(m,3H),6.88(d,J =2.3Hz,1H),4.19(dt,J=29.9,5.8Hz,4H),3.63(dd,J=11.4,6.3Hz,4H),2.43–2.29(m,4H). 13 C NMR (101MHz, CDCl 3)δ: 175.85, 163.00, 158.69, 157.90, 152.12, 130.20, 127.90, 124.89, 124.48, 118.59, 114.76, 114.59, 100.76, 65.94, 65.37, 32.33, 31.98, 30.Calc.92, 29 21 h 20 Br 2 o 4 :C50.83,H4.06;Found C50.78,H4.05.MS(ESI):m / z[M-Br] + calcd415.1, found414.9.

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Abstract

The invention relates to a 7,4'-disubstituted isoflavone derivative and a preparation method and application thereof. The structural formula is shown in the specification, wherein R is 2-hydroxyl-3-di-n-propylaminly propyl, 2-hydroxyl-3-piperidyl propyl, 3-dimethylamino propyl or 3-diethylin propyl. The preparation method of the compound is simple and high in yield. The compound prepared according to the invention has good antitumor activity in vitro.

Description

technical field [0001] The invention relates to 7,4'-disubstituted isoflavone derivatives and a preparation method and application thereof, belonging to the field of medicinal chemistry. technical background [0002] As a kind of phytoestrogens, isoflavones have a series of physiological activities. It has a certain therapeutic effect on breast cancer, colon cancer, lung cancer, prostate cancer, skin cancer and leukemia, and can also prevent the occurrence of ovarian cancer, colon cancer, gastric cancer and prostate cancer. The antitumor activity data of the compounds involved in the existing structure-activity relationship research shows that the antitumor activity of most synthetic derivatives is not significantly improved compared with isoflavones themselves, so it can be seen that the antitumor activity of isoflavones has not been greatly improved. good development. [0003] The present invention uses tivolone as a control drug, which has obvious inhibitory effect on v...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/36A61K31/352A61K31/453A61P35/00
Inventor 胡先明周丁山庹伟刘鹏肖玉玲周小菊
Owner WUHAN UNIV