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Trifluoromethyl pyrimidine derivatives containing Schiff base structural unit, and preparation method and application thereof

A technology of trifluoromethylpyrimidine and structural units, which is applied in the field of medicinal chemistry and can solve problems such as drugs that cannot satisfy patients

Active Publication Date: 2020-05-22
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the developed drugs are far from meeting the needs of patients. Therefore, the research and development of anti-tumor drugs with high efficiency and low toxicity has far-reaching significance.

Method used

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  • Trifluoromethyl pyrimidine derivatives containing Schiff base structural unit, and preparation method and application thereof
  • Trifluoromethyl pyrimidine derivatives containing Schiff base structural unit, and preparation method and application thereof
  • Trifluoromethyl pyrimidine derivatives containing Schiff base structural unit, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0031] The preparation of embodiment 1 (E)-4-(2-phenylene dihydrazine)-2-(prop-2-yn-1-ylthio)-6-(trifluoromethyl)pyrimidine (5a)

[0032] At room temperature, 2-mercapto-6-(trifluoromethyl)pyrimidin-4-ol (1.95g, 10mmol) was dissolved in potassium hydroxide (0.67g, 12.05mmol) in N,N-dimethylformyl (20ml) amine solution, slowly drop in propyne bromide (940ul, 12.05mmol), heat up to 80°C for a substitution reaction, TLC detects that the reaction is complete, cool the reaction solution to room temperature, add to the ice-water mixture and stir, there are a lot of pale A yellow solid was precipitated, filtered with suction, washed with water 3-4 times, and dried to obtain the compound 3-(prop-2-yn-1-ylthio)-5-(trifluoromethyl)phenol.

[0033] Pale yellow solid, yield 83.5%; 1 H NMR (400MHz, DMSO-d 6 )δ7.29(s,1H),5.19(d,J=2.3Hz,2H),4.82(d,J=2.3Hz,1H). 13 C NMR (101MHz, DMSO-d 6 )δ170.89, 168.65, 163.40, 159.39, 155.72, 155.37, 155.02, 154.66, 73.40, 55.37, 20.59, 19.17. HR-MS (E...

Embodiment 2

[0040] Example 2 (E)-4-(2-(3-fluorobenzylidene)hydrazino)-2-(prop-2-yn-1-ylthio)-6-(trifluoromethyl)pyrimidine Preparation of (5b)

[0041] At room temperature, (3-(prop-2-yn-1-ylsulfanyl)-5-(trifluoromethyl)phenyl)(0.15g, 0.609mmol)hydrazine was added to 6ml of absolute ethanol, and the temperature was raised to 80 DEG C, slowly add 3-fluorobenzaldehyde (60.97ul, 0.609mmol), TLC detects that the reaction is complete, the reaction solution is cooled to room temperature, and carries out column chromatography (V 石油醚 :V 乙酸乙酯 =6:1), the eluent was concentrated to obtain the product.

[0042] White solid, yield 74.0%; 1 H NMR (400MHz, DMSO-d 6 )δ 1 H NMR (400MHz, DMSO) δ12.26(s, 1H), 8.21(s, 1H), 7.67(d, J=9.8Hz, 1H), 7.59(d, J=7.8Hz, 1H), 7.49(dt ,J=13.8,6.9Hz,1H),7.34(s,1H),7.30–7.23(m,1H),3.99(d,J=2.6Hz,2H),3.18(t,J=2.6Hz,1H) . 13 C NMR (101MHz, DMSO-d 6 )δ169.92, 163.66, 162.15, 161.23, 144.41, 136.43, 130.88, 130.79, 123.59, 116.89, 116.68, 113.10, 112.88, 96.17, 79.8...

Embodiment 3

[0043] Example 3 (E)-4-(2-(4-fluorobenzylidene)hydrazino)-2-(prop-2-yn-1-ylthio)-6-(trifluoromethyl)pyrimidine Preparation of (5c)

[0044] Replace 3-fluorobenzaldehyde with 4-fluorobenzaldehyde, and the preparation method is the same as in Example 2.

[0045] White solid powder, yield 62.4%; 1 H NMR (400MHz, DMSO-d 6 )δ12.19(s,1H),8.22(s,1H),8.05–8.00(m,4H),7.33(s,1H),4.00(d,J=2.5Hz,2H),3.19(t,J =2.6Hz,1H). 13 C NMR (101MHz, DMSO-d 6 )δ170.09,161.97,152.63,147.84,141.66,127.28,124.40,122.01,119.16,117.08,114.31,95.70,79.91,73.40,61.18,55.75,18.57. 15 h 11 f 4 N 4 S[M+H] + :355.0641,found:355.0642.

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Abstract

The invention belongs to the field of medicinal chemistry, and discloses Schiff base structural unit-containing trifluoromethyl pyrimidine derivatives with antitumor activity, and a preparation methodand application thereof. The compounds have structures as shown in a general formula I which is described in the specification. In the general formula I, R is a benzaldehyde group, a substituted benzaldehyde group, a 9-anthraaldehyde group or a 3-indole formaldehyde group. Results of in-vitro anti-tumor activity evaluation show that the series of derivatives have obvious inhibiting and killing effects on various tumor cells. The derivatives can be further optimized and developed into novel drugs to be applied to clinical prevention and treatment of cancers.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to pyrimidine derivatives, in particular to trifluoromethylpyrimidine derivatives with anti-tumor activity based on Schiff base structural units and their preparation methods and applications. Background technique [0002] Tumor is one of the most common and serious diseases that threaten human life and health in the world today. There are many anti-tumor drugs currently on the market, and pyrimidine compounds exhibit a wide range of biological activities, such as: anti-cancer, anti-bacterial, anti-inflammatory and anti-convulsant. Excellent representatives of its anti-tumor activity are: erlotinib (Erlotinib), lapatinib (lapatinib), etc. However, the developed drugs are far from meeting the needs of patients. Therefore, the research and development of anti-tumor drugs with high efficiency and low toxicity has far-reaching significance. Schiff bases have special physiological activ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47C07D409/12C07D401/12C07D403/12A61P35/00
CPCC07D239/47C07D409/12C07D401/12C07D403/12A61P35/00
Inventor 张秋荣刘宏民张佩刘秀娟王涛张洋刘丽敏汪正捷栗娜陈秀英郑甲信周蕊赵培荣
Owner ZHENGZHOU UNIV
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