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Distyrene compound containing bromothiazole ring as well as synthesis method and application thereof

A technology of stilbene and thiazole ring, which is applied in the field of -5-bromo-4--2-substituted styryl thiazole compounds, can solve the problems of structure and biological activity that have not been reported in literature and the like, and achieves the preparation of simple effect

Active Publication Date: 2018-11-23
ZHEJIANG UNIV OF TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The series of (E)-5-bromo-4-(2,6-difluorophenyl)-2-substituted styrylthiazoles designed and synthesized by the present invention have no literature reports on their structure and biological activity

Method used

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  • Distyrene compound containing bromothiazole ring as well as synthesis method and application thereof
  • Distyrene compound containing bromothiazole ring as well as synthesis method and application thereof
  • Distyrene compound containing bromothiazole ring as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Synthesis of Derivative Ia (R(n)=H):

[0032]Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 15 mL (86.8 mmol) of triethyl phosphite, heat to reflux, and detect the reaction by TLC , and the reaction was complete after about 1 h. Concentrate to remove excess triethyl phosphite to obtain a concentrated solution; add 20 mL of DMF, benzaldehyde (1.3 g, 12 mmol) and sodium hydroxide (0.9 g, 22 mmol) to the obtained concentrated solution to react. The reaction process was detected by TLC, and the reaction was completed in about 3 hours. The reaction solution was poured into 150 mL of ice water, stirred, and a solid precipitated, filtered, and then recrystallized with ethyl acetate to obtain 1.6 g of a yellow solid, which was (E)-4 -(2,6-difluorophenyl)-2-styrylthiazole, the calculated yield is 54.7%. m.p.: 79~80℃;

[0033] 1 H NMR (500 MHz, Chloroform- d ) δ 7.56 (d, J = 7.5 Hz, 2H), 7.50 – 7.37(m, 5H), 7.37 – 7.26 (m, 2H), 7.02 (t, ...

Embodiment 2

[0038] Example 2 Synthesis of derivative Ib (R(n)=o-chloro):

[0039] Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 9.0 mL (50.0 mmol) triethyl phosphite, heat to reflux, and detect the reaction by TLC , and the reaction was completed after about 1.5 h. Concentrate to remove excess triethyl phosphite to obtain a concentrated solution; add 25 mL of DMF, o-chlorobenzaldehyde (1.4 g, 10 mmol) and sodium hydroxide (1.3 g, 32 mmol) to the obtained concentrated solution to react. The reaction process was detected by TLC, and the reaction was completed in about 3.5 hours. The reaction solution was poured into 150 mL of ice water, stirred, and a solid was precipitated, filtered, and then recrystallized with ethanol to obtain 1.4 g of a yellow solid, which was (E)-4-( 2,6-difluorophenyl)-2-o-chlorostyrylthiazole, the calculated yield is 40.6%. m.p.: 87~89℃;

[0040] 1 H NMR (500 MHz, Chloroform- d ) δ 7.83 (d, J = 16.0 Hz, 1H), 7.74 – 7.67(dd, J = 7....

Embodiment 3

[0045] Example 3 Synthesis of derivative Ic (R(n)=p-chloro):

[0046] Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 12 mL (69.5 mmol) of triethyl phosphite, heat to reflux, and detect the reaction by TLC , and the reaction was completed after about 3 h. Concentrate to remove excess triethyl phosphite to obtain a concentrated solution; add 22 mL of DMF, p-chlorobenzaldehyde (2.8 g, 20 mmol) and sodium hydroxide (2.0 g, 50 mmol) to the obtained concentrated solution to react. The reaction process was detected by TLC, and the reaction was completed in about 2.5 hours. The reaction solution was poured into 150 mL of ice water, stirred, and a solid was precipitated, filtered, and then recrystallized with n-hexane to obtain 1.9 g of a yellow solid, namely (E)-4- (2,6-difluorophenyl)-2-p-chlorostyrylthiazole, the calculated yield is 56.1%. m.p.: 91~93℃;

[0047] 1 H NMR (500 MHz, Chloroform- d ) δ 7.50 – 7.45 (m, 3H), 7.40 (d, J = 16.0Hz, 1H), 7.38 –...

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Abstract

The invention discloses a distyrene compound containing a bromothiazole ring as well as a synthesis method and application thereof. The compound has the following synthesis process that firstly, 2-(brome methyl)-4-(2,6-difluorophenyl) thiazole and triethyl phosphite react in a backflow state; TLC monitoring is performed till reaction completion; concentration is performed to remove excessive triethyl phosphite; solvents DMF, sodium hydroxide and substituted benzaldehyde are added into the obtained concentrated solution; reaction is performed at room temperature; after the reaction is completed, post treatment is performed to obtain a distyrene compound containing a thiazole ring; next, the distyrene compound containing the thiazole ring and N-bromo-succinimide take bromo reaction in acetonitrile solvents at 0 to 100 DEG C; the distyrene compound containing the bromothiazole ring is obtained. By using the technology, a kind of novel (E)-5-brome-4-(2,6-difluorophenyl)-2-substituted styryl thiazole compounds can be obtained through synthesis. The preparation of the compound is simple; certain anticancer and anti-fungus activity is shown.

Description

technical field [0001] The present invention relates to ( E )-5-bromo-4-(2,6-difluorophenyl)-2-substituted styrylthiazole compounds and applications thereof. Background technique [0002] As phytoalexins, stilbene compounds widely exist in nature, such as Polygonaceae plants Veratrum, Polygonum multiflorum, Polygonum cuspidatum, Liliaceae Smilax plants Smilax, Cassia, mulberry roots, etc. Stilbene compounds from natural sources have a variety of biological activities and have attracted widespread attention. They play a very important role in the field of new drug research and development. For example, in the field of medicine, it has anti-tumor (J Agr Food Chem, 2011, 59(16): 8632-8638), improvement of body immunity (BBA-Biomembranes, 1985, 837(2): 209-212), anti-inflammatory ( J Agr Food Chem, 2017, 65(51):11179-11191), anti-HIV (J Pharm Sci, 2004, 93(10): 2448-2457) and other activities; it has insecticidal properties in the field of pesticides (Chem PharmBull, 1992, 40...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/32A61P35/00A61P31/10A01N43/78A01P3/00
CPCA01N43/78A61P31/10A61P35/00C07D277/32
Inventor 翁建全章俊辉周智勇周亮朱亚波刘幸海
Owner ZHEJIANG UNIV OF TECH
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