1-<2-(3,4-dimethoxyphenethyl)>imidazolidine-2,4,5-trione | 92764-05-1

• 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: 1-<2-(3,4-dimethoxyphenethyl)>imidazolidine-2,4,5-trione
• 英文别名: 1-[2-(3,4-Dimethoxyphenyl)ethyl]imidazolidine-2,4,5-trione
• CAS: 92764-05-1
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: VVEOVSAWSBFUGE-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C(Solv: ethanol (64-17-5))
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<2-(3,4-dimethoxyphenethyl)>imidazolidine-2,4,5-trione 在 sodium tetrahydroborate 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4,5-(3,4-dimethoxybenzo)-1,8-diazabicyclo<4.3.0>nonane-7,9-dione
  参考文献：
  名称：

  Synthesis of substituted 2-imidazolidinones and annelated hydantoins via amidoalkylation transformations

  摘要：

  DOI：

  10.1021/jo00199a001
• 作为产物：
  描述：

  2-(3,4-二甲氧基苯基) 乙胺盐酸盐 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 1-<2-(3,4-dimethoxyphenethyl)>imidazolidine-2,4,5-trione
  参考文献：
  名称：

  Highly Selective Aldose Reductase Inhibitors. 1. 3-(Arylalkyl)-2,4,5-trioxoimidazolidine-1-acetic Acids

  摘要：

  A series of 3-(arylalkyl)-2,4,5-trioxoimidazolidine-1-acids (1) was prepared and tested for aldose reductase (AR) and aldehyde reductase (ALR) inhibitory activities. These compounds showed strong inhibitory activity against AR without significant inhibitory activity for ALR. The ratio of IC50(ALR)/IC50(AR) was > 1000 in some compouds. On the basis of pharmacological tests such as the recovery of reduced motor nerve conduction velocity and toxicological profile, 3-(3-nitrobenzyl)-2,4,5-trioxoimidazolidine-1-acid (NZ-314) was selected as the candidate for clinical development.

  DOI：

  10.1021/jm9508393

文献信息

• LIAO, ZENG-KUN;KOHN, H., J. ORG. CHEM., 1984, 49, N 25, 4745-4752
  作者：LIAO, ZENG-KUN、KOHN, H.

  DOI：——

  日期：——
• Highly Selective Aldose Reductase Inhibitors. 1. 3-(Arylalkyl)-2,4,5-trioxoimidazolidine-1-acetic Acids
  作者：Akira Ishii、Takayuki Kotani、Yasuhiro Nagaki、Yoji Shibayama、Yoshio Toyomaki、Nobuhisa Okukado、Kazuharu Ienaga、Kaoru Okamoto

  DOI：10.1021/jm9508393

  日期：1996.1.1

  A series of 3-(arylalkyl)-2,4,5-trioxoimidazolidine-1-acids (1) was prepared and tested for aldose reductase (AR) and aldehyde reductase (ALR) inhibitory activities. These compounds showed strong inhibitory activity against AR without significant inhibitory activity for ALR. The ratio of IC50(ALR)/IC50(AR) was > 1000 in some compouds. On the basis of pharmacological tests such as the recovery of reduced motor nerve conduction velocity and toxicological profile, 3-(3-nitrobenzyl)-2,4,5-trioxoimidazolidine-1-acid (NZ-314) was selected as the candidate for clinical development.
• Synthesis of substituted 2-imidazolidinones and annelated hydantoins via amidoalkylation transformations
  作者：Zeng Kun Liao、Harold Kohn

  DOI：10.1021/jo00199a001

  日期：1984.12