2-[N'-(4-hydroxy-3-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[N'-(4-hydroxy-3-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-[2-[(4-hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]-4-methyl-1,3-thiazole-5-carboxylate
• 化学式: C₁₅H₁₇N₃O₄S
• 分子量: 335.384
• InChiKey: VZZHFEFHMHCYCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  香草醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-[N'-(4-hydroxy-3-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives

  摘要：

  A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-(4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidenelhydrazin-1-yl]-mu 3-thiazol-5-yliethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 mu M and 0.648 mu M respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl)thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 mu M and 631.84 mu M respectively. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2013.11.001

文献信息

• Discovery of potent anti-tuberculosis agents targeting leucyl-tRNA synthetase
  作者：Olga I. Gudzera、Andriy G. Golub、Volodymyr G. Bdzhola、Galyna P. Volynets、Sergiy S. Lukashov、Oksana P. Kovalenko、Ivan A. Kriklivyi、Anna D. Yaremchuk、Sergiy A. Starosyla、Sergiy M. Yarmoluk、Michail A. Tukalo

  DOI：10.1016/j.bmc.2016.01.028

  日期：2016.3

  the discovery of small-molecule inhibitors of M. tuberculosis LeuRS. Using receptor-based virtual screening we have identified six inhibitors of M. tuberculosis LeuRS from two different chemical classes. The most active compound 4-[4-(4-Bromo-phenyl)-thiazol-2-yl]hydrazonomethyl}-2-methoxy-6-nitro-phenol (1) inhibits LeuRS with IC50 of 6 μM. A series of derivatives has been synthesized and evaluated

  结核病是由人类病原菌结核分枝杆菌引起的严重传染病。细菌耐药性是当今非常重要的医学问题，具有不同作用机理的新型抗生素的开发是现代医学的重要目标。亮氨酰tRNA合成酶（LeuRS）最近已在临床上被验证为抗微生物靶标。在这里，我们报告结核分枝杆菌LeuRS小分子抑制剂的发现。使用基于受体的虚拟筛选，我们从两种不同的化学类别中鉴定了六种结核分枝杆菌LeuRS抑制剂。最具活性的化合物4-[[4-（4-溴-苯基）-噻唑-2-基]肼基甲基} -2-甲氧基-6-硝基苯酚（1）以6μM的IC 50抑制LeuRS 。已经合成了一系列衍生物，并在体外针对结核分枝杆菌LeuRS进行了评估。结果表明，活性最高的化合物2,6-二溴-4-[4-（4-硝基-苯基）-噻唑-2-基]-肼基甲基}-苯酚抑制LeuRS，IC 50为2.27μM 。测试所有活性化合物对结核分枝杆菌H37Rv的抗菌作用。化合物1似乎具有最佳的细胞通透性，并抑制病原菌的生长，IC
• In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives
  作者：Parameshwar Makam、Prasoon Kumar Thakur、Tharanikkarasu Kannan

  DOI：10.1016/j.ejps.2013.11.001

  日期：2014.2

  A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-(4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidenelhydrazin-1-yl]-mu 3-thiazol-5-yliethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 mu M and 0.648 mu M respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl)thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 mu M and 631.84 mu M respectively. (C) 2013 Elsevier B.V. All rights reserved.