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1, 3-thiazole derivative

A technology for thiazole rings and compounds, applied in the field of 2-substituted 1,3-thiazole derivatives and their synthesis, can solve problems such as cumbersome operations and restrictions on the types of substituent groups

Inactive Publication Date: 2013-08-07
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the synthetic methods of 2-amido-1,3-thiazole derivatives provided in the current literature are cumbersome and the types of substituent groups are limited.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0090] Embodiment 1——preparation formula IVa (R 1 = Ph, R 2 =4-CF 3 -Ph,R 3 =Et) compound:

[0091]

[0092] IVa

[0093] Under the protection of nitrogen, add 1mmol phenylacetylene to a 20mL reaction tube containing 2mL ether, use a dry ice-acetone bath to keep the reaction temperature at -78°C, add 1mmol n-butyllithium dropwise, and react for half an hour after the addition is complete. Add 0.125mmol S 8 , naturally warming up to 25°C, and reacting with magnetic stirring for two hours. Under nitrogen protection, 1 mmol of N-tert-butyl-N-ethylcarbodiimide and 1 mmol of p-trifluoromethylbenzoyl chloride were added to a 20 mL reaction tube filled with 3 mL of diethyl ether, and reacted at 25° C. for 48 h. The above two reaction solutions were mixed and reacted at 80° C. for 10 hours. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether:dichloromethane=1:1 was used as an eluent to obtain a thia...

Embodiment 2

[0094] Embodiment 2——preparation formula IVb (R 1 =2-Me-Ph, R 2 =4-CF 3 -Ph, R 3 =Et) compound:

[0095]

[0096] IVb

[0097] Under the protection of nitrogen, add 1mmol of o-methylphenylacetylene to a 20mL reaction tube containing 2mL of ether, use a dry ice-acetone bath to keep the reaction temperature at -78°C, add 1mmol of n-butyllithium dropwise, and react after the addition is complete. Half an hour, add 0.125mmol S 8 , naturally warming up to 25°C, and reacting with magnetic stirring for two hours. Under nitrogen protection, 1 mmol of N-tert-butyl-N-ethylcarbodiimide and 1 mmol of p-trifluoromethylbenzoyl chloride were added to a 20 mL reaction tube filled with 3 mL of diethyl ether, and reacted at 25° C. for 48 h. The above two reaction solutions were mixed and reacted at 60° C. for 10 hours. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether:dichloromethane=1:1 was used as an elue...

Embodiment 3

[0098] Embodiment 3——preparation formula IVc (R 1 =3-Cl-Ph,R 2 =4-CF 3 -Ph,R 3 =Et) compound:

[0099]

[0100] IVc

[0101] Under nitrogen protection, add 1mmol m-chlorophenylacetylene to a 20mL reaction tube containing 2mL ether, use a dry ice-acetone bath to keep the reaction temperature at -78°C, add 1mmol n-butyllithium dropwise, and react halfway after the addition is complete. hour, add 0.125mmol S 8 , naturally warming up to 25°C, and reacting with magnetic stirring for two hours. Under nitrogen protection, 1 mmol of N-tert-butyl-N-ethylcarbodiimide and 1 mmol of p-trifluoromethylbenzoyl chloride were added to a 20 mL reaction tube filled with 3 mL of diethyl ether, and reacted at 25° C. for 48 h. The above two reaction solutions were mixed and reacted at 100° C. for 10 hours. The reaction solution was concentrated, decolorized and separated on a silica gel column, and a mixed solvent of petroleum ether:dichloromethane=1:1 was used as an eluent to obtain a th...

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Abstract

The invention provides a 1, 3-thiazole derivative and a synthesis method thereof. A 2-acylamino thiazole derivative is prepared from carbodiimide, acyl chloride, a terminal alkyne compound and elemental sulfur. The yield is higher, and the synthesis method is scientific and reasonable, so that a universal method for synthesizing the 2-acylamino thiazole derivative with various substituent groups is provided. The method has the advantages that the raw materials are easily available, and the application range is large, the separating rate is high, experimental devices and operations are simple and easy to operate; therefore, the 1, 3-thiazole derivative can be further developed and used.

Description

technical field [0001] In the field of medicinal chemistry, the invention specifically relates to a 1,3-thiazole derivative, in particular to a 2-substituted 1,3-thiazole derivative and a synthesis method thereof. Background technique [0002] 1,3-Thiazole derivatives have multiple uses in the field of organic synthesis and are common synthetic intermediates. [0003] Among them, 2-amidothiazole compounds have antibacterial, anti-cancer and anti-tumor activities, and can be used as protein kinase inhibitors. They are also used as chemokine receptors and anti-adenosine receptors in the field of medicine. Narcotic effect. [0004] As described below, 2-amidothiazole compounds have been reported to have antibacterial, anticancer and antitumor applications. [0005] "Ureas of 5-Aminopyrazole and 2-Aminothiazole Inhibit Growth of Gram-Positive Bacteria. Bioorg. Med. Chem. Lett. 2003, 13, 4463" describes that 2-aminopyrazole can inhibit the growth of Gram-Positive Bacteria. "Sy...

Claims

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Application Information

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IPC IPC(8): C07D277/46C07D417/04A61P31/00A61P35/00A61P23/00
Inventor 张文雄王杨迟樾席振峰
Owner PEKING UNIV
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