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

Received Date: 26 August 2015
Available Online: 1 February 2016
Fund Project: 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)

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.
- thiazoline-thiazole,
- crystal structure,
- annulation,
- antibacterial activities
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