(Z)-3-(4-ethylphenyl)-2-((Z)-(4-oxo-2-thioxothiazolidin-5-ylidene)methyl)acrylonitrile | 1556921-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-3-(4-ethylphenyl)-2-((Z)-(4-oxo-2-thioxothiazolidin-5-ylidene)methyl)acrylonitrile
• 英文别名: (Z)-3-(4-ethylphenyl)-2-[(Z)-(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]prop-2-enenitrile
• CAS: 1556921-67-5
• 化学式: C₁₅H₁₂N₂OS₂
• 分子量: 300.405
• InChiKey: YOWBMLPXTJKKBF-AJDRMPRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[(4-Ethylphenyl)-hydroxymethyl]prop-2-enenitrile 在 sodium nitrate 、 1-己基-3-甲基咪唑硫酸氢盐 、 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 (Z)-3-(4-ethylphenyl)-2-((Z)-(4-oxo-2-thioxothiazolidin-5-ylidene)methyl)acrylonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs)

  摘要：

  Baylis-Hillman chemistry derived four series of new epalrestat analogues were synthesized. Three structural changes are introduced in these 39 new epalrestat analogues synthesized. All compounds were evaluated for their in vitro aldose reductase inhibitory (ALR) activity. Biological activity data indicates that compounds 6, 16, 19, 28 and 29 are potent and the activity is in the range of reference drug, epalrestat. Molecular modelling studies were performed to understand the binding interactions of these active molecules with the ALR protein. Molecular docking data indicates the key interactions of epalrestat were retained in some of the active compounds whereas some new interactions were noticed for other molecules. The modifications introduced on epalrestat have impact for developing a new-type of ALR inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.043

文献信息

• Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs)
  作者：Thatikonda Narendar Reddy、Mettu Ravinder、Pankaj Bagul、Keerthi Ravikanti、Chandrakant Bagul、Jagadeesh Babu Nanubolu、Kolupula Srinivas、Sanjay K. Banerjee、Vaidya Jayathirtha Rao

  DOI：10.1016/j.ejmech.2013.10.043

  日期：2014.1

  Baylis-Hillman chemistry derived four series of new epalrestat analogues were synthesized. Three structural changes are introduced in these 39 new epalrestat analogues synthesized. All compounds were evaluated for their in vitro aldose reductase inhibitory (ALR) activity. Biological activity data indicates that compounds 6, 16, 19, 28 and 29 are potent and the activity is in the range of reference drug, epalrestat. Molecular modelling studies were performed to understand the binding interactions of these active molecules with the ALR protein. Molecular docking data indicates the key interactions of epalrestat were retained in some of the active compounds whereas some new interactions were noticed for other molecules. The modifications introduced on epalrestat have impact for developing a new-type of ALR inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.