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Stilbene analogue containing thiazole ring structure and synthesis method and application thereof

A synthesis method and a technology containing a thiazole ring can be applied in the fields of drug combination, resistance to vector-borne diseases, organic chemistry, etc., and can solve the problems of structure and biological activity that have not been reported in literature, and achieve the effect of simple preparation process.

Active Publication Date: 2019-11-05
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The series of stilbene analogs containing thiazole ring structure designed and synthesized by the present invention have no literature reports on their structure and biological activity research

Method used

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  • Stilbene analogue containing thiazole ring structure and synthesis method and application thereof
  • Stilbene analogue containing thiazole ring structure and synthesis method and application thereof
  • Stilbene analogue containing thiazole ring structure and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Synthesis of Compound Ia (R(n)=H):

[0028]Add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10 mmol) and triethyl phosphite (2.5 g, 15 mmol) into a 100 mL three-necked flask, and heat to The reaction was carried out at 100°C, and the progress of the reaction was detected by TLC, and the reaction was completed after about 3 hours. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (2.9 g, 40 mmol), benzaldehyde (1.1 g, 10 mmol) and sodium hydroxide (0.4 g, 10 mmol) 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 (120 mL), stirred, and a solid was precipitated, filtered, and the filter cake was recrystallized with ethyl acetate to obtain 1.9 g of a yellow solid, which was (E) -5-bromo-4-(4-fluorophenyl)-2-styrylthiazole, the calculated yield is 5...

Embodiment 2

[0031] The synthesis of embodiment 2 compound Ib (R (n)=o-chloro):

[0032] Add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10 mmol) and triethyl phosphite (3.3 g, 20 mmol) into a 100 mL three-necked flask, heat The reaction was carried out at 120°C, and the progress of the reaction was detected by TLC, and the reaction was completed after about 1.5 h. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (4.0 g, 55 mmol), o-chlorobenzaldehyde (1.4 g, 10 mmol) and sodium hydroxide (1.3 g, 32 mmol ) react at room temperature. The reaction process was detected by TLC, and the reaction was completed in about 4.5 hours. Then, the reaction solution was poured into ice water (130 mL), stirred, and a solid precipitated, filtered, and the filter cake was recrystallized with n-hexane to obtain 1.86 g of a yellow solid, which was (E) -2-(2-chlorostyryl)-5-bromo-4-(4-fluorophenyl)thiazole, the calculated yield is 47.3%. m.p.: 124~12...

Embodiment 3

[0035] Example 3 Synthesis of Compound Ic (R(n)=p-chloro):

[0036] Add 5-bromo-2-(bromomethyl)-4-(4-fluorophenyl)thiazole (3.7 g, 10 mmol) and triethyl phosphite (2.8 g, 17 mmol) into a 100 mL three-necked flask, and heat to The reaction was carried out at 130°C, and the progress of the reaction was detected by TLC, and the reaction was completed after about 1 h. Concentrate and remove excess triethyl phosphite to obtain a concentrated solution; add DMF (3.7g, 50mmol), p-chlorobenzaldehyde (1.7g, 12 mmol) and sodium hydroxide (0.9 g, 22 mmol) 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 (185 mL), stirred, and a solid precipitated, filtered, and the filter cake was recrystallized with n-hexane to obtain 2.4 g of a yellow solid, namely (E)- 2-(4-chlorostyryl)-5-bromo-4-(4-fluorophenyl)thiazole, the calculated y...

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Abstract

The invention discloses a Stilbene analogue containing a thiazole ring structure and a synthesis method and application thereof. The structural formula of the Stilbene analogue containing a thiazole ring structure is shown as a formula (I), wherein in the formula (I), H on a benzene ring is mono-substituted, disubstituted or unsubstituted by substituents R; n is an integer greater than or equal to0 and smaller than or equal to 2 and represents the number of the substituents R on the benzene ring; when n is equal to 0, it indicates that H on the benzene ring is not substituted; when n is equalto 1, it indicates that H on the benzene ring is mono-substituted by the substituents R; when n is equal to 2, H on the benzene ring is disubstituted by the substituents R, and the substituents R atdifferent substitution positions are the same or different; the substituents R are selected from hydrogen, C1-C4 alkyl, C1-C3 haloalkyl and C1-C3 alkoxy or halogen. The provided Stilbene analogue containing the thiazole ring structure is simple in preparation process and shows certain anti-tumor activity.

Description

technical field [0001] The invention relates to a Stilbene analogue containing a thiazole ring structure and a synthesis method and application thereof. Background technique [0002] Stilbene compounds are a general term for a class of compounds with stilbene as the structural core. They exist widely in nature as phytoalexins, such as Maimaiteng, Liliaceae veratrum, Liaceae Polygonum cuspidatum, Polygonum multiflorum, and Mulberry Mulberries, Grapes, etc. Stilbene compounds have a wide range of biological activities and have attracted widespread attention. In the field of medicine, they have antibacterial and anti-inflammatory (J. Agric. Food Chem, 2017, 65(51): 11179-11191), antioxidant (Chem. Pharm. bull, 1987, 35(2): 887-890.), anticancer (Mol. Nutr. & Food Res, 2005, 49(5):452-461.), antitumor (Anticancer Res, 2004, 24 (5A): 2783-2840.), anti-cardiovascular disease (Medical Review, 2010, 16(6), 937-939), inhibition of thrombosis (Platelets, 2005, 16(5): 251-260); In t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/32A61P35/00
CPCC07D277/32A61P35/00Y02A50/30
Inventor 翁建全叶飞霞朱亚波谭成侠
Owner ZHEJIANG UNIV OF TECH
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