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Trifluoromethylpyrimidine derivatives containing Schiff base structural unit and preparation method and use thereof

A technology of trifluoromethylpyrimidine and structural unit, which is applied in the field of medicinal chemistry and can solve problems such as the inability of drugs to satisfy patients

Active Publication Date: 2022-08-02
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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  • Trifluoromethylpyrimidine derivatives containing Schiff base structural unit and preparation method and use thereof
  • Trifluoromethylpyrimidine derivatives containing Schiff base structural unit and preparation method and use thereof
  • Trifluoromethylpyrimidine derivatives containing Schiff base structural unit and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 (E) Preparation of 4-(2-phenylenedihydrazine)-2-(prop-2-yn-1-ylthio)-6-(trifluoromethyl)pyrimidine (5a)

[0032] 2-Mercapto-6-(trifluoromethyl)pyrimidin-4-ol (1.95 g, 10 mmol) was dissolved in potassium hydroxide (0.67 g, 12.05 mmol) in N,N-dimethylformyl at room temperature (20ml) in the amine solution, slowly add bromopropyne (940ul, 12.05mmol) dropwise, be warming up to 80 ℃ to take place substitution reaction, TLC detects that the reaction is completed, the reaction solution is cooled to room temperature, added in the ice-water mixture and stirred, there is a large amount of light 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-ylsulfanyl)-5-(trifluoromethyl)phenol.

[0033] Light 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 )δ170.89,168.65,163.40,159.39,155.72,155.37,155.02,1...

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) (0.15 g, 0.609 mmol) hydrazine was added to 6 ml of absolute ethanol, and the temperature was raised to 80 ° C, slowly add 3-fluorobenzaldehyde (60.97ul, 0.609mmol), TLC detection reaction is completed, the reaction solution is cooled to room temperature, and column chromatography (V 石油醚 : V 乙酸乙酯 =6:1), concentrate the eluent 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 )δ169.92,163.66,162.15,161.23,144.41,136.43,130.88,130.79,123.59,116.89,116.68,113.10,112.88,96.17,79.88,73.44,18.57.HR-MS(ESI)Calcd for ...

Embodiment 3

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

[0044] Substitute 3-fluorobenzaldehyde with 4-fluorobenzaldehyde, and the preparation method is the same as that 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.HR-MS(ESI):Calcd for CSI 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 a Schiff base structural unit-containing trifluoromethylpyrimidine derivative with antitumor activity and a preparation method and application thereof. The compounds of the present invention have the general formula I structure. In vitro anti-tumor activity evaluation found that the series of compounds have obvious inhibitory and killing effects on various tumor cells. It can be applied to the preparation of clinical drugs for prevention and treatment of cancer. I.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to pyrimidine derivatives, in particular to trifluoromethylpyrimidine derivatives containing Schiff base structural units with antitumor activity and a preparation method and application thereof. Background technique [0002] Cancer is one of the most common and serious diseases that endanger human life and health in the world today. There are many anti-tumor drugs currently on the market, and pyrimidine compounds show a wide range of biological activities, such as: anti-cancer, anti-bacterial, anti-inflammatory and anti-convulsant. The excellent representatives of its anti-tumor activity are: erlotinib, lapatinib and so on. 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 activities such as ...

Claims

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Application Information

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Patent Type & Authority Patents(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