2-[(2-hydroxy-benzylidene)-hydrazino]-4-methyl-thiazole-5-carboxylic acid ethyl ester | 52481-56-8

• 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-[(2-hydroxy-benzylidene)-hydrazino]-4-methyl-thiazole-5-carboxylic acid ethyl ester
• 英文别名: 2-o-Hydroxybenzylidenhydrazino-4-methyl-5-carbethoxythiazol；Ethyl 2-[2-[(2-hydroxyphenyl)methylidene]hydrazinyl]-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 52481-56-8
• 化学式: C₁₄H₁₅N₃O₃S
• 分子量: 305.357
• InChiKey: ATCLBIWNPGMWSG-UHFFFAOYSA-N

物化性质

• 沸点：
  467.1±55.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 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：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 生成 2-[(2-hydroxy-benzylidene)-hydrazino]-4-methyl-thiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  2-(2-苄亚肼基)噻唑-5-羧酸酯及其制备方法 与医药用途

  摘要：

  本发明公开了结构式Ⅰ所示的2‑(2‑苄亚肼基)噻唑‑5‑羧酸酯衍生物及其药学上可接受的盐，其制备方法和药物组合物以及其在制备流感病毒神经氨酸酶抑制剂中的应用。其中，R选自：C1～C2、C3～C4直链或C3～C4支链烷基；R1选自：氢、C1～C2烷基、C3～C4直链或支链烷基、三氟甲基；X1、X5选自：氢、氘、C1～C2烷基、羟基、甲氧基、乙氧基、氟、氯、溴、碘、硝基；X2、X4选自：氢、氘、C1～C2烷基、C3～C4直链或支链烷基、羟基、甲氧基、乙氧基、氟、氯、溴、碘、硝基；X3选自：氢、氘、C1～C2烷基、羟基、甲氧基、乙氧基、氟、氯、溴、碘、硝基、羧基或烷氧羰基。

  公开号：

  CN105777664B

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.