Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

Citation: TANG Li-Juan, QIAN Bao-Hua, MA Gui-Zhen, LIU Wei-Wei. Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole[J]. Chinese Journal of Structural Chemistry, 2016, 35(4): 645-650. doi: 10.14102/j.cnki.0254-5861.2011-0957 shu

Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

1.
Pharmacy School, Jiangsu Key Laboratory of Marie Biotechnology, Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, Huaihai Institute of Technology, Lianyungang 222005, China
基金项目:
This project was supported by the Open-end Funds of Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology (2013HS004) (2013HS004)

Open-end Funds of Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening (2015HYB05) (2015HYB05)

a project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (201402) (201402)

摘要: 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole, a novel compound, was synthesized by the annulation of 5-hydroxyethylcarbamoyl-4-methyl-2-(4-methylphenyl)-1,3-thiazole with P₂S₅. 5-Hydroxyethylcarbamoyl-4-methyl-2-(4-methylphenyl)-1,3-thiazole was prepared from the starting material of p-tolunitrile. The newly synthesized compounds were characterized by elemental analysis, IR, NMR (¹H, ¹³C) and MS spectra. Hence, the crystal of the title compound was obtained, and its structure was determined by X-ray diffraction analysis. The crystal belongs to the triclinic system, space group P1 with a=7.354(4), b=8.383(4), c=11.543(6) Å, α=76.688(6), β=72.299(6), γ=88.157(6)°, V=659.2(6) Å³, Z=2, M_r=274.39, Dc=1.382 g/cm³, μ=0.386 mm^-1, F(000)=288, R=0.0586 and wR=0.1808 for 2984 unique reflections with 2213observed ones (I > 2σ(I)). The title compound was also screened for its antibacterial activities against Bacillus subtilis and Escherichia coli. The result indicates that the target compound presents potential antimicrobial activities, and that the minimum inhibitory concentration (MIC) values of the title compound against the two tested strains are both 62.5 μg/mL.

关键词:

English

Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

1.
Pharmacy School, Jiangsu Key Laboratory of Marie Biotechnology, Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, Huaihai Institute of Technology, Lianyungang 222005, China
Received Date: 26 August 2015
Fund Project:

Abstract: 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole, a novel compound, was synthesized by the annulation of 5-hydroxyethylcarbamoyl-4-methyl-2-(4-methylphenyl)-1,3-thiazole with P₂S₅. 5-Hydroxyethylcarbamoyl-4-methyl-2-(4-methylphenyl)-1,3-thiazole was prepared from the starting material of p-tolunitrile. The newly synthesized compounds were characterized by elemental analysis, IR, NMR (¹H, ¹³C) and MS spectra. Hence, the crystal of the title compound was obtained, and its structure was determined by X-ray diffraction analysis. The crystal belongs to the triclinic system, space group P1 with a=7.354(4), b=8.383(4), c=11.543(6) Å, α=76.688(6), β=72.299(6), γ=88.157(6)°, V=659.2(6) Å³, Z=2, M_r=274.39, Dc=1.382 g/cm³, μ=0.386 mm^-1, F(000)=288, R=0.0586 and wR=0.1808 for 2984 unique reflections with 2213observed ones (I > 2σ(I)). The title compound was also screened for its antibacterial activities against Bacillus subtilis and Escherichia coli. The result indicates that the target compound presents potential antimicrobial activities, and that the minimum inhibitory concentration (MIC) values of the title compound against the two tested strains are both 62.5 μg/mL.

Key words:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

English

Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

English

Synthesis, Crystal Structure and Antibacterial Activities of 4-Methyl-2-(4-methylphenyl)-5-(2-thiazolinyl)-1,3-thiazole

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs