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A kind of 2-amino-4,5-diarylthiazole type compound and its preparation method and application

A technology of thiazole type and compound, which is applied to 2-amino-4,5-diarylthiazole type compound and the field of preparation method and application thereof, can solve the problems of low bioavailability, drug resistance, high toxicity and the like, Achieving a good inhibitory effect

Inactive Publication Date: 2018-02-09
南京信卓化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many anti-tumor drugs currently used clinically have many disadvantages, such as high toxicity, low bioavailability, and drug resistance.

Method used

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  • A kind of 2-amino-4,5-diarylthiazole type compound and its preparation method and application
  • A kind of 2-amino-4,5-diarylthiazole type compound and its preparation method and application
  • A kind of 2-amino-4,5-diarylthiazole type compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of 4-(5-methoxy-2,2-dimethyl-2H-benzopyran-8-yl)-5-phenylthiazol-2-amine (1)

[0030]

[0031] Step 1: Add 1-(2-hydroxy-4-methoxyphenyl)ethanone (4.85g, 10mmol) to 100mL CH 3 After CN was dissolved, cooled to 0°C in an ice bath, and slowly added DBU (1.5mL, 15mmol), CuCl 2 (4.03mg, 0.3%mmol), 3-chloro-3-methyl-1-butyne (1.53g, 15mmol), reacted in ice bath for 5h, TLC monitoring showed that the reaction was complete. Stop the reaction, add 1N dilute hydrochloric acid dropwise to adjust pH=2, remove CH under reduced pressure 3 CN, the residue was poured into 50mL water, a large amount of solids were precipitated, filtered, and dried as solid powder, the yield was 85%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 1.75 (s, 6H), 2.58 (s, 3H), 2.69(s, 1H), 3.84 (s, 3H), 6.58 (dd, 1H), 7.19 (d, 1H) , 7.75 (d, 1H); EIMS m / z =233.28 [M + ].

[0032] Step 2: Suspend 1-(4-methoxy-2-((2-methyl-3-yn-2-yl)oxo)phenyl)ethanone (2.32 g, 10 mmol) in 50 mL of pyridine ...

Embodiment 2

[0040] Example 2: Preparation of 5-phenyl-4-(2,2,5-trimethyl-2H-benzopyran-8-yl)thiazol-2-amine (2)

[0041]

[0042] The yield is 80%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 1.50 (s, 6H), 2.54 (s, 3H), 5.96(d, 1H), 6.67 (s, 2H), 6.79 (d, 1H), 6.88 (d, 1H), 7.42 (d, 1H), 7.45-7.56(m, 3H), 7.75-7.86(m, 2H); EIMS m / z = 349.46 [M + ].

Embodiment 3

[0043] Example 3: Preparation of 4-(5-ethyl-2,2-dimethyl-2H-benzopyran-8-yl)-5-phenylthiazol-2-amine (3)

[0044]

[0045] Yield 83%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 1.35 (t, 3H), 1.52 (s, 6H), 2.84(q, 2H), 5.98 (d, 1H), 6.83 (d, 1H), 6.87 (d, 1H), 6.97 (s, 2H), 7.43 (d,1H), 7.46-7.58 (m, 3H), 7.70-7.81 (m, 2H); EIMS m / z = 363.49 [M + ].

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Abstract

The invention discloses a 2-amino-4,5-diaryl-thiazole-type compound and a preparing method and application thereof. The 2-amino-4,5-diaryl-thiazole-type compound has the structure shown in the formula (I) (please see the specification). The preparing method includes the steps that substituted 2-hydroxyacetophenone serves as a raw material, and is etherified, rearranged, brominated, subjected to ring closing through thiourea, and reacted with phthalic anhydride, the reacted product is brominated to obtain substituted 2-(5-bromine-4-(2,2-dimethyl-2H-chromene-8-base) thiazole-2-base) isoindoline-1,3-diketone, the substituted 2-(5-bromine-4-(2,2-dimethyl-2H-chromene-8-base) thiazole-2-base) isoindoline-1,3-diketone and arylboronic acid are coupled to obtain substituted 2-(4-(2,2-dimethyl-2H-chromene-8-base)-5-aryl thiazole-2-base) isoindoline-1,3-diketone, and finally protection is removed to obtain the target compound. The 2-amino-4,5-diaryl-thiazole-type compound can serve as a raw material of antitumor medicine, and raw materials of the preparing method are simple and easy to obtain, and operation is convenient.

Description

technical field [0001] The invention relates to a 2-amino-4,5-diarylthiazole compound, a preparation method thereof and an application as a tubulin inhibitor in the preparation of antitumor drugs. Background technique [0002] At present, malignant tumors have become a common and frequently-occurring disease that seriously endangers human health. Every year, 7.6 million new cases of malignant tumors are discovered in the world. It is the second leading cause of human death, second only to cardiovascular and cerebrovascular diseases. Moreover, the incidence of tumors is increasing year by year. The World Health Organization (WHO) predicts that 1.2 million people will die of cancer in 2030. Among the 27 tumor types, lung cancer, gastric cancer, liver cancer, colon cancer and breast cancer caused the most deaths. Due to the increasing tumor mortality, it is necessary to discover new, safe and efficient drugs to treat and prevent tumors. However, many anticancer drugs currentl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04A61K31/427A61P35/00
CPCC07D417/04
Inventor 王广成彭知云王静邓斌李文标
Owner 南京信卓化工科技有限公司
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