3-amino-4-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)methylene)-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide | 1604810-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-amino-4-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)methylene)-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide
• CAS: 1604810-49-2
• 化学式: C₂₀H₁₅ClN₆OS
• 分子量: 422.898
• InChiKey: HWLPLACBMBIRRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102.53
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5-(4-Chlorophenyl)-2-phenylpyrazole-3-carbaldehyde 、 氨基硫脲 、 氰乙酸乙酯 在 bleaching earth clay 作用下， 反应 4.0h， 以74.6%的产率得到3-amino-4-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)methylene)-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Development of novel pyrazolone derivatives as inhibitors of aldose reductase: An eco-friendly one-pot synthesis, experimental screening and in silico analysis

  摘要：

  Aldose reductase is the key enzyme of polypol pathway leading to accumulation of sorbitol. Sorbitol does not diffuse across the cell membranes easily and therefore accumulates within the cell, causing osmotic damage which leads to retinopathy (cataractogenesis), neuropathy and other diabetic complications. Currently, aldose reductase inhibitors like epalrestat, ranirestat and fidarestat are used for the amelioration of diabetic complications. However, such drugs are effective in patients having good glycemic control and less severe diabetic complications. In present study we have designed novel pyrazolone derivative and performed eco-friendly synthesis approach and tested the synthesized compounds as potential inhibitors of aldose reductase activity. Additional in silico analysis in current study indicates presence of highly conserved chemical environment in active site of goat lens aldose reductase. The reported data is expected to be useful for developing novel pyrazolone derivatives as lead compounds in the management of diabetic complications. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.02.002