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4-(4-halogenated phenyl)-2-(substituted styryl) thiazole compound and application thereof

A technology of styryl and halogenated phenyl, which is applied in the field of 4--2-thiazole compounds, can solve the problems of structure and biological activity that have not been reported in literature, and achieve the effect of simple preparation process

Inactive Publication Date: 2020-11-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] A 4-(4-halophenyl)-2-(substituted styryl)thiazole compound designed and synthesized by the present invention has no literature reports on its structure and biological activity research

Method used

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  • 4-(4-halogenated phenyl)-2-(substituted styryl) thiazole compound and application thereof
  • 4-(4-halogenated phenyl)-2-(substituted styryl) thiazole compound and application thereof
  • 4-(4-halogenated phenyl)-2-(substituted styryl) thiazole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 compound Ia (X=Br, R(n)=hydrogen):

[0026]Add 2-(bromomethyl)-4-(4-bromophenyl)thiazole (3.3g, 10mmol) and triethyl phosphite (4.1g, 25mmol) into a 100mL three-necked flask, heat to 140°C for reaction, TLC The progress of the reaction was detected, and the reaction was completed after about 4 hours. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (2.9g, 40mmol), benzaldehyde (1.1g, 10mmol) and sodium hydroxide (0.4g, 10mmol) to the resulting concentrated solution at room temperature reaction. The reaction process was detected by TLC, and the reaction was completed in about 4 hours. Then, the reaction solution was poured into ice water (110 mL), stirred, and a solid precipitated, filtered, and the filter cake was recrystallized with ethyl acetate to obtain 1.76 g of a yellow solid, which was (E)- 4-(4-Bromophenyl)-2-styrylthiazole, the calculated yield was 51.4%. m.p.:168~170℃;

[0027] 1 H N...

Embodiment 2

[0028] Synthesis of Example 2 Compound Ib (X=Br, R(n)=o-methoxy):

[0029] Add 2-(bromomethyl)-4-(4-bromophenyl)thiazole (3.3g, 10mmol) and triethyl phosphite (4.1g, 25mmol) into a 100mL three-necked flask, heat to 145°C for reaction, TLC The progress of the reaction was detected, and the reaction was completed after about 4 hours. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (4.0g, 55mmol), o-methoxybenzaldehyde (1.36g, 10mmol) and sodium hydroxide (1.3g, 32mmol) to the resulting concentrated solution ) react at room temperature. The reaction process was detected by TLC, and the reaction was completed in about 3.5 hours. Then, the reaction solution was poured into ice water (130 mL), stirred, and solids were precipitated, filtered, and the filter cake was weighed with a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:2. Crystallization gave 2.02 g of a yellow solid, namely (E)-4-(4-bromophenyl)-2-(2-methox...

Embodiment 3

[0031] Synthesis of Example 3 Compound Ic (X=Br, R(n)=m-methoxy):

[0032] Add 2-(bromomethyl)-4-(4-bromophenyl)thiazole (3.3g, 10mmol) and triethyl phosphite (5.0g, 30mmol) into a 100mL three-necked flask, heat to 150°C for reaction, TLC The progress of the reaction was detected, and the reaction was completed after about 5 hours. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (3.7g, 50mmol), m-methoxybenzaldehyde (1.63g, 12mmol) and sodium hydroxide (0.9g, 22mmol) to the resulting concentrated solution ) react at room temperature. The reaction process was detected by TLC, and the reaction was completed in about 4 hours. Then, the reaction solution was poured into ice water (165 mL), stirred, and a solid precipitated, filtered, and the filter cake was recrystallized with ethyl acetate to obtain 1.8 g of a yellow solid, which was (E)- 4-(4-Bromophenyl)-2-(3-methoxystyryl)thiazole, the calculated yield was 48.3%. m.p.:112~113℃;

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Abstract

The invention discloses a 4-(4-halophenyl)-2-(substituted styryl)-thiazole compound and application thereof. A structural formula of the compound is shown as (I), the preparation process of the seriesof compounds is simple, and the series of compounds show certain antitumor activity, have certain inhibitory activity on DNA topoisomerase. Meanwhile, the compound has very strong cytotoxicity to human breast cancer cells and human colon cancer cells. In the formula (I), X on a halogenated benzene ring is Cl or Br, and H on the benzene ring is mono-substituted, di-substituted or not substituted by a substituent R; substituent groups R at different substituent positions are the same or different; wherein the substituent group Rs are a C1-C4 alkyl group, a C1-C3 halogenated alkyl group, a C1-C3alkoxy group or halogen.

Description

technical field [0001] The invention relates to a 4-(4-halophenyl)-2-(substituted styryl)thiazole compound and its application. Background technique [0002] Stilbenes, that is, stilbenes, is a general term for a class of substances with a stilbene core or its polymers. It is mainly distributed in the xylem parenchyma of plants, and is a response to plant damage from pests or other adverse stimuli. Stimulant products (synthesis and structural modification of stilbene compounds with biological activity [D]. Nanjing: Nanjing University of Science and Technology, 2005). Natural stilbene compounds widely exist in nature, such as Polygonaceae plants such as stilbee, veratrum, Polygonum cuspidatum, Liliaceae mulberry root, Cassia, and foods such as grapes, pineapples, and peanuts. At the same time, it also widely exists in artificially synthesized compounds and is an important drug synthesis intermediate. According to literature reports, it has a wide range of biological activit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/22C07D277/24A61P15/14A61P35/00A61K31/426
CPCA61P15/14A61P35/00C07D277/22C07D277/24
Inventor 翁建全叶飞霞孙晓彤刘幸海
Owner ZHEJIANG UNIV OF TECH
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