(E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as preparation method and application thereof

A trifluoromethyl and styrene-based technology, which is applied in the field of medicine, can solve problems that have not been seen, and achieve the effects of good yield, simple and feasible preparation method, and excellent anti-proliferation ability

Active Publication Date: 2021-06-08
中国医科大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, this patent designs and synthesizes a new type of anti-tumor compound, while retaining the effective active group of mulitinib, and introducing the structure of indole and aniline, in order to obtain a new compound with more anti-tumor effect. report on the structure and provide new ideas for drug design

Method used

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  • (E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as preparation method and application thereof
  • (E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as preparation method and application thereof
  • (E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1 Preparation of (E)-N-((2-(4-(trifluoromethyl)styryl)oxazol-4-yl)methyl)aniline (A1).

[0063] a. Preparation of (E)-3-(4-(trifluoromethyl)phenyl)acrylic acid.

[0064] In the 500mL reaction flask, add 1 times the amount (molar amount) 4-(trifluoromethyl) benzaldehyde (30g, 0.17mol), 2 times the amount of pyridine (27.26g, 0.34mol), 1.5 times the amount of malonic acid (26.89 g, 0.25mol), piperidine 10mL, and isopropanol 200mL as solvent, reacted at 90°C, and monitored the reaction progress by thin-layer chromatography. After the reaction was completed, the isopropanol was removed by evaporation under reduced pressure, and water was added to the reaction solution, and the pH value was adjusted to 2. After standing still, the solid was precipitated, and the filter cake was obtained as the product by suction filtration, with a yield of 93.5%.

[0065] b. Preparation of (E)-3-(4-(trifluoromethyl)phenyl)acryloyl chloride.

[0066] Add 1 times the amount of (E)-3-...

Embodiment 2

[0073] Example 2 Preparation of (E)-2-fluoro-N-((2-(4-(trifluoromethyl)styryl)oxazol-4-yl)methyl)aniline (A2).

[0074] The preparation method is the same as (A1).

[0075] White solid, yield: 78.2%. 1 HNMR (600MHz, DMSO-d 6 )δ7.97(s,1H),7.92(d,J=8.0Hz,2H),7.74(d,J=8.0Hz,2H),7.55(d,J=16.5Hz,1H),7.29(d, J=16.4Hz, 1H), 7.02(dd, J=12.1, 8.2Hz, 1H), 6.95(t, J=7.7Hz, 1H), 6.77(t, J=8.5Hz, 1H), 6.56(d, J=5.2Hz, 1H), 5.88(s, 1H), 4.27(d, J=5.9Hz, 2H); 13 CNMR (150MHz, DMSO-d 6 )δ160.11,151.78,149.89,140.43,139.13,136.26,136.14,136.04,133.66,127.81,125.43,124.49,116.46,115.77,114.24,114.09,112.20,38.76;MS(ESI,m / z):363.1122[M+ H] + .

Embodiment 3

[0076] Example 3 Preparation of (E)-3-fluoro-N-((2-(4(trifluoromethyl)styryl)oxazol-4-yl)methyl)aniline (A3).

[0077] The preparation method is the same as (A1).

[0078] White solid, yield: 73.1%. 1 HNMR (600MHz, DMSO-d 6)δ7.97(s,1H),7.89(d,J=6.9Hz,2H),7.71(d,J=8.0Hz,2H),7.54(d,J=16.4Hz,1H),7.31(d, J=10.4Hz, 1H), 7.08(t, J=7.4Hz, 1H), 6.67(d, J=7.7Hz, 2H), 6.55(t, J=7.1Hz, 1H), 6.05(s, 1H) ,4.19(s,2H); 13 CNMR (150MHz, DMSO-d 6 )δ160.31, 160.17, 150.23, 140.15, 139.04, 136.75, 136.27, 133.70, 130.02, 127.79, 125.41, 116.39, 108.42, 101.95, 101.78, 98.46, 136.26, 45.93 m / z H] +

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Abstract

The invention belongs to the technical field of medicines, relates to a compound with anti-tumor activity and a specific chemical structure, and in particular relates to an (E)-4-methyl-2-(4-(trifluoromethyl) styryl) oxazole compound as well as a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R1 group is substituted by a 2-position, 3-position or 4-position mono-substituted fluorine atom, methyl, chlorine atom, methoxy group, bromine atom or an unsubstituted group; and the R2 group is substituted by a 2-position, 3-position or 4-position mono-substituted methoxy group, a chlorine atom or an unsubstituted group. Pharmacological studies show that the compound has certain inhibitory activity on human non-small cell lung cancer A549 cells, can be used for preparing anti-tumor drugs, and opens up a new way for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a class of compounds with specific chemical structures having antitumor activity, in particular to (E)-4-methyl-2-(4-(trifluoromethyl)styryl)oxazoles Antitumor compound and its preparation method and application. Background technique [0002] Malignant tumors remain difficult-to-treat diseases today and represent a serious global public health problem. The anti-tumor drugs currently on the market all have side effects in varying degrees, and there are also defects in the selectivity of the drugs. Therefore, the synthesis of highly efficient new anticancer drugs is one of the hotspots of modern medicinal chemistry research. Therefore, this patent designs and synthesizes a new type of anti-tumor compound, while retaining the effective active group of mulitinib, and introducing the structure of indole and aniline, in order to obtain a new compound with more anti-tumor effect. The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32C07D413/06A61P35/00A61K31/421A61K31/422
CPCC07D263/32C07D413/06A61P35/00
Inventor 孟繁浩朱菊钱欣画薛文涵李帅李馨阳刘凯利王德普
Owner 中国医科大学
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