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N-(2-chloro-6-methyl phenyl)-2-(phenyl acrylamide)thiazole-5-formamide derivative, and preparation method and use thereof

A technology of phenylacrylamide and methylphenyl, which is applied in the field of its preparation, N--2-thiazole-5-carboxamide derivatives, can solve the problems of white blood cell concentration surge and uncontrollable growth of white blood cells, and achieve obvious inhibitory effect , novel structure and high yield

Inactive Publication Date: 2012-07-25
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This change in stem cell DNA gives malignant cells an advantage over normal stem cell growth and survival, resulting in an uncontrolled growth of white blood cells that, if left untreated, can lead to a surge in white blood cell concentration

Method used

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  • N-(2-chloro-6-methyl phenyl)-2-(phenyl acrylamide)thiazole-5-formamide derivative, and preparation method and use thereof
  • N-(2-chloro-6-methyl phenyl)-2-(phenyl acrylamide)thiazole-5-formamide derivative, and preparation method and use thereof
  • N-(2-chloro-6-methyl phenyl)-2-(phenyl acrylamide)thiazole-5-formamide derivative, and preparation method and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1N-(2-chloro-6-methylphenyl)-2-(3,4-dimethylphenylacrylamide)thiazole-5-carboxamide

[0034]

[0035] synthetic route:

[0036]

[0037] 1. Preparation of intermediate 1-3,4-dimethylphenylacrylic acid

[0038] Add 1.34g (10.0mmol) of 3,4-dimethylbenzaldehyde, 2.08g (20.0mmol) of malonic acid, 8mL of pyridine and 0.5mL of piperidine respectively in a 100mL three-necked flask, and heat the oil bath to reflux temperature for reaction. After 6 hours, thin-layer chromatography (TLC) was used to detect that 3,4-dimethylbenzaldehyde had reacted completely (developing solvent is the solvent obtained by mixing ethyl acetate, sherwood oil and glacial acetic acid in a volume ratio of 1:6:1), Stop the reaction, add 8 mL of toluene to the reaction system, then add K 2 CO 3solution, adjust the pH to 9-10, stir for 30 minutes, then separate the liquid to retain the water layer, adjust the pH to 3 with 1mol / L HCl, at this time, a large amount of white solid precipit...

Embodiment 2

[0044] Embodiment 2N-(2-chloro-6-methylphenyl)-2-(3,5-dimethoxyphenylacrylamide)thiazole-5-carboxamide

[0045]

[0046] The operating steps are the same as in Example 1, except that in step 1, 3,5-dimethoxybenzaldehyde is used instead of 3,4-dimethylbenzaldehyde. The target product is a white solid with a melting point of 309-310°C and a yield of 92.1%.

[0047] 1 H NMR (400MHz, DMSO-d 6 )δ: 12.64 (s, 1H), 10.07 (s, 1H), 8.32 (s, 1H), 7.68-7.75 (d, 1H, J=15.8Hz), 7.24-7.43 (m, 3H), 6.82-6.96 (m, 3H), 6.6 (d, 1H, J=4.4Hz), 3.8 (s, 6H), 2.27 (s, 3H).

Embodiment 3

[0048] Example 3N-(2-chloro-6-methylphenyl)-2-(3-trifluoromethylphenylacrylamide)thiazole-5-carboxamide

[0049]

[0050] The operating steps are the same as in Example 1, except that in step 1, 3-trifluoromethylbenzaldehyde is used instead of 3,4-dimethylbenzaldehyde. The target product is a white solid with a melting point of 284-286°C and a yield of 92.5%.

[0051] 1 H NMR (400MHz, DMSO-d 6 )δ: 12.60(s, 1H), 10.01(s, 1H), 8.31(s, 1H), 7.78-8.05(m, 4H), 7.68-7.75(d, 1H), 7.2-7.45(m, 3H) , 7.03-7.08 (d, 1H, J=15.9Hz), 2.27 (s, 3H).

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Abstract

The invention discloses an N-(2-chloro-6-methyl phenyl)-2-(phenyl acrylamide)thiazole-5-formamide derivative, and a preparation method of the derivative and use of the derivative, wherein the general structural formula of the N-(2-chloro-6-methyl phenyl)-2-(phenyl acrylamide)thiazole-5-formamide derivative is as follows: wherein R1, R2, R3 and R4 are independently selected from hydrogen, chlorine, fluorine, methyl, methoxyl or trifluoromethyl; at least two of R1, R2, R3 and R4 are hydrogen. In comparison with the existing anti-leukemia drug dasatinib, the compound disclosed by the invention has remarkable inhibitory effect on K562 leukemia cells and is suitable for being further chosen as an anti-leukemia drug; the condition required for synthesis of the compound is mild, and the yield of the compound is high.

Description

1. Technical field [0001] The present invention relates to a kind of pharmaceutical compound, specifically a kind of N-(2-chloro-6-methylphenyl)-2-(phenylacrylamide) thiazole-5-carboxamide derivative, its preparation method and its use. 2. Background technology [0002] Chronic myeloid leukemia (CML) is an acquired hematopoietic stem cell malignant clonal proliferation disease caused by acquired changes in the DNA of a stem cell in the bone marrow. This change in stem cell DNA gives malignant cells an advantage over normal stem cells for growth and survival, resulting in an uncontrolled growth of white blood cells that, if left untreated, can lead to a surge in white blood cell concentration. Approximately 100,000 CML patients develop the disease each year. Clinically, CML can be divided into chronic phase, accelerated phase and blast phase. The clinical and blood manifestations of acute leukemia in patients are called CML blast. The survival period of most patients is 3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56A61K31/426A61P35/02
Inventor 姚日生陈磊祥陆小琴邓胜松阮班锋何红波
Owner HEFEI UNIV OF TECH
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