1-{4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazol-5-yl}ethan-1-one | 1489265-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-{4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazol-5-yl}ethan-1-one
• 英文别名: 1-[4-methyl-2-[(2E)-2-[1-(2-pyridyl)ethylidene]hydrazino]thiazol-5-yl]ethanone；1-[4-methyl-2-[(2E)-2-(1-pyridin-2-ylethylidene)hydrazinyl]-1,3-thiazol-5-yl]ethanone
• CAS: 1489265-26-0
• 化学式: C₁₃H₁₄N₄OS
• 分子量: 274.346
• InChiKey: DYBJAZJOMGWGMU-LZYBPNLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-乙酰基吡啶 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 1-{4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazol-5-yl}ethan-1-one
  参考文献：
  名称：

  2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

  摘要：

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.054

文献信息

• 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.