2-(N'-benzylidenehydrazino)-4-methylthiazole-5-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(N'-benzylidenehydrazino)-4-methylthiazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(2-benzylidenehydrazinyl)-4-methyl-1,3-thiazole-5-carboxylate
• 化学式: C₁₄H₁₅N₃O₂S
• 分子量: 289.358
• InChiKey: QBCSKDDXCWSUIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-(N'-benzylidenehydrazino)-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

• Facial one-pot, three-component synthesis of thiazole compounds by the reactions of aldehyde/ketone, thiosemicarbazide and chlorinated carboxylic ester derivatives
  作者：Ma Xiabing、Keyume Ablajan、Mamateli Obul、Mengnisa Seydimemet、Reyhangul Ruzi、Li Wenbo

  DOI：10.1016/j.tet.2016.03.053

  日期：2016.5

  An efficient, clean and environmentally benign reaction process was developed for the convenient and cheap synthesis of hydrazone derivatives. A series of novel thiazole compounds were synthesized via one-pot three-component reaction of aldehyde/ketone, thiosemicarbazide, and chlorinated β-keto ester catalyzed by anhydrous sodium acetate. The reactions had excellent yields in EtOH solvent. The synthetic

  为了方便和廉价地合成衍生物，开发了一种有效，清洁和环境友好的反应方法。通过醛/酮，硫代氨基脲和无水乙酸钠催化的氯化β-酮酯的一锅三组分反应合成了一系列新型噻唑化合物。该反应在EtOH溶剂中具有优异的产率。讨论了合成方法和反应机理。