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A stilbene-like compound containing a thiazole ring and its synthesis method and application

A stilbene and thiazole ring-containing technology is applied in organic chemistry, drug combination, antineoplastic drugs, etc. It can solve the problems of structure and biological activity that have not been reported in the literature, and achieve the effect of simple preparation

Active Publication Date: 2022-03-01
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The series of stilbene-like compounds containing thiazole rings designed and synthesized by the present invention have no literature reports on their structures and biological activities.

Method used

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  • A stilbene-like compound containing a thiazole ring and its synthesis method and application
  • A stilbene-like compound containing a thiazole ring and its synthesis method and application
  • A stilbene-like compound containing a thiazole ring and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of Derivative Ia (R(n)=H):

[0030] 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℃;

[0031] 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

[0033] Example 2 Synthesis of derivative Ib (R(n)=o-chloro):

[0034]Add 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole (2.9 g, 10 mmol) into 9.0 mL (50.0 mmol) of 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 for reaction. 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℃;

[0035] 1 H NMR (500 MHz, Chloroform- d ) δ 7.83 (d, J = 16.0 Hz, 1H), 7.74 –7.67 (dd, J...

Embodiment 3

[0037] Example 3 Synthesis of derivative Ic (R(n)=p-chloro):

[0038] 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℃;

[0039] 1 H NMR (500 MHz, Chloroform- d ) δ 7.50 – 7.45 (m, 3H), 7.40 (d, J =16.0 Hz, 1H), 7.38 –...

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Abstract

The invention discloses a stilbene-like compound containing a thiazole ring, its synthesis method and application. The synthesis method of this type of compound is as follows: first react 2-(bromomethyl)-4-(2,6-difluorophenyl)thiazole and triethyl phosphite under reflux state, and TLC monitors until after the reaction ends , concentrated to remove excess triethyl phosphite to obtain a concentrated solution; add solvent DMF, sodium hydroxide and substituted benzaldehyde to the concentrated solution, react at room temperature, monitor by TLC until the end of the reaction, and finally obtain thiazole-containing Cyclic stilbene-like compounds. A new class of stilbene-like compounds containing a thiazole ring obtained in the present invention is simple to prepare and exhibits certain anti-tumor activity. In the examples, the anti-tumor activity of the synthesized compound was measured by DNA loosening experiment , DNA loosening test results show that most of the compounds have a certain anti-tumor activity at a concentration of 50 μM, and the inhibitory activity of compound Il on TOP I (DNA topoisomerase) reaches about 70%.

Description

technical field [0001] The invention relates to a stilbene-like compound containing a thiazole ring, a synthesis method and application 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 (Bioorgan Med Chem, 2008, 16(7): 3800-3808), anti-oxidation (JBiol Chem, 2001, 276(25): 22586-22594), 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 (ChemPharmBull, 1992, 40(5): 1130-1136), antifungal ...

Claims

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Application Information

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IPC IPC(8): C07D277/22C07D277/24A61P35/00
CPCA61P35/00C07D277/22C07D277/24
Inventor 翁建全徐雯秀周智勇周亮朱亚波刘幸海
Owner ZHEJIANG UNIV OF TECH
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