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Thiazole derivative, and synthesis method and application thereof

A synthesis method and technology of derivatives, applied in the fields of drug combination, organic chemistry, antitumor drugs, etc., can solve the problems of low yield, dangerous reagents, high temperature, etc., and achieve the effects of good yield, environmental friendliness, and simple reaction process.

Inactive Publication Date: 2016-08-17
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, under the action of metals, alkalis or microwaves, thiazole derivatives can be obtained, but the prior art has the disadvantages of high temperature, dangerous reagents, and low yield.

Method used

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  • Thiazole derivative, and synthesis method and application thereof
  • Thiazole derivative, and synthesis method and application thereof
  • Thiazole derivative, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Synthesis of 3-benzyl-2-thio-2,3-dihydro-thiazole-5-benzophenone

[0044]

[0045] α-Bromoamine enone compound, base and solvent are respectively selected from (Z)-3-(benzylamino)-2-bromo-1-phenyl-2-en-1-one, K 2 CO 3 , dimethyl sulfoxide (DMSO), the amount of raw material is (Z)-3-(benzylamino)-2-bromo-1-phenyl-2-en-1-one 0.3mmol, 2.0eq.K 2 CO 3 , solvent 3mL, and reacted at 80° C. for 1.5 hours to obtain the target product formula (IA), brown liquid, and the separation yield was 76%.

[0046] NMR data: 1 H NMR (400MHz, CDCl 3 , TMS) δ5.38(s,2H),7.30-7.39(m,5H),7.43-7.47(m,2H),7.52(s,1H),7.56-7.58(m,1H),7.68(d, J = 7.2Hz, 2H); 13 CNMR (100MHz, CDCl 3 , TMS): δ52.93, 126.76, 128.33, 128.63, 128.99, 129.03, 129.41, 133.25, 134.52, 136.82, 138.02, 184.46, 191.04; HRMS (EI) calcd for C 17 h 13 ONS 2 m + :311.0439,found 311.0443.

[0047] High-resolution mass spectrometry data: HRMS(EI)calcd for C 17 h 13 ONS 2 m + :311.0439,found 311.0443.

...

Embodiment 2

[0052] Example 2: Synthesis of 3-benzyl-2-thio-2,3-dihydro-thiazole-5-(4-bromophenyl)-methanone

[0053]

[0054]

[0055] α-Bromoamine enone compound, base, and solvent are respectively selected from (Z)-3-(benzylamino)-2-bromo-1-(4-bromophenyl)-2-en-1-one, K 2 CO 3 , dimethylsulfoxide (DMSO), the amount of raw material is (Z)-3-(benzylamino)-2-bromo-1-(4-bromophenyl)-2-en-1-one 0.3mmol, 2.0 equivalent K 2 CO 3 , solvent 3mL, and reacted at 80° C. for 2.5 hours to obtain the target product formula (IB), a brown liquid, and the separation yield was 62%.

[0056] NMR data: 1 H NMR (400MHz, CDCl 3 , TMS) δ5.38(s, 2H), 7.32-7.41(m, 5H), 7.48(s, 1H), 7.55(d, J=8.8Hz, 2H), 7.60(d, J=8.4Hz, 2H ); 13 CNMR (100MHz, CDCl 3 , TMS): δ53.06, 126.30, 128.38, 128.47, 129.19, 129.57, 130.16, 132.44, 134.51, 135.65, 137.97, 183.34, 191.11;

[0057] High-resolution mass spectrometry data: HRMS(EI)calcd for C 17 h 12 Brons 2 m + :388.9544, found 388.9547.

Embodiment 3

[0058] Example 3: Synthesis of 3-benzyl-2-thio-2,3-dihydro-thiazole-5-(4-chlorophenyl)-methanone

[0059]

[0060] α-Bromoamine ketene compound, base and solvent are respectively selected from (Z)-3-(benzylamino)-2-bromo-1-(4-chlorophenyl)-2-en-1-one, K 2 CO 3 , dimethyl sulfoxide (DMSO), the amount of raw material is (Z)-3-(benzylamino)-2-bromo-1-(4-chlorophenyl)-2-en-1-one 0.3mmol, 2.0 equivalent K 2 CO 3 , solvent 3mL, reacted at 80°C for 3.5 hours to obtain the target product formula (IC), a brown liquid, and the separation yield was 69%;

[0061] NMR data: 1 H NMR (400MHz, CDCl 3 , TMS) δ5.38(s, 2H), 7.31-7.44(m, 7H), 7.51(s, 1H), 7.63(d, J=8.4Hz, 2H); 13 CNMR (100MHz, CDCl 3 ,TMS): δ53.00, 126.31, 128.41, 129.11, 129.40, 129.50, 130.04, 134.47, 135.13, 137.99, 139.78, 183.14, 191.00;

[0062] High-resolution mass spectrometry data: HRMS(EI)calcd for C 17 h 12 ClONS 2 m + :345.0049, found 345.0045.

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Abstract

The invention discloses a thiazole derivative represented by formula (I), and a synthesis method thereof. The thiazole derivative represented by formula (I) is synthesized through a reaction of an alpha-bromoenaminone compound and carbon disulfide used as raw materials in a solvent under the action of an alkali. Like compounds have good bioactivities, such as antibacterial activity and anti-breast cancer activity. The synthesis method has the advantages of simple and easily available raw materials, good universality, simple post-treatment, good yield and environmental protection. The invention also discloses an application of the thiazole derivative represented by formula (I) in the field of medicines.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and specifically relates to a thiazole derivative and its synthesis method and application. Background technique [0002] Thiazoles are an important class of organic compounds, which are the main structural units in many drugs, and most of them have strong biological activities. It has important application value in the fields of medicine, dyes, pesticides, etc., and also has important research significance in medicinal chemistry and natural product chemistry. Therefore, much attention has been paid to the synthesis research of thiazoles, which are drugs with antibacterial and antibreast cancer activities. At present, there are many reports on the synthesis methods of such compounds, and great progress has been made. For example, thiazole derivatives can be obtained under the action of metals, alkalis or microwaves, but the prior art has disadvantages such as high temper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/36C07D417/06A61P31/00A61P35/00A61P11/00
CPCC07D277/36C07D417/06
Inventor 李艳忠李艳丽陶相华张芳芳周园园姚其义郑重赵育磊孔令凯
Owner EAST CHINA NORMAL UNIV
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