1-(m-methoxybenzyl)imidazolidine-2,4,5-trione | 92764-08-4

• 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-(m-methoxybenzyl)imidazolidine-2,4,5-trione
• 英文别名: 1-(3-methoxybenzyl)imidazolidinetrione；1-[(3-Methoxyphenyl)methyl]imidazolidine-2,4,5-trione
• CAS: 92764-08-4
• 化学式: C₁₁H₁₀N₂O₄
• mdl: MFCD12862911
• 分子量: 234.211
• InChiKey: DJWLYVPRBMBDOO-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C(Solv: methanol (67-56-1))
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(m-methoxybenzyl)imidazolidine-2,4,5-trione 在 盐酸 、 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.5h， 生成 3-Carboxymethyl-1-(3-methoxybenzyl)parabanic acid
  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
• 作为产物：
  描述：

  3-甲氧基苯甲胺盐酸盐 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 1-(m-methoxybenzyl)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

• A pharmaceutical composition containing an imidazolidinetrione derivative or pharmaceutically acceptable salt thereof
  申请人：NIPPON ZOKI PHARMACEUTICAL CO. LTD.

  公开号：EP0194226A1

  公开（公告）日：1986-09-10

  Pharmaceutical compositions contain as an active ingredient oxaluric acid derivatives of the formula (I): wherein each of R, and R2, which may be the same or different, represents hydrogen or an alkyl or cycloalkyl group or the group and each of R3 and R4, which may be the same or different, represents hydrogen, halogen, a nitro group or a lower alkyl or lower alkoxy group, and pharmaceutically acceptable salts and metal complexes thereof. The compositions have hypoglycemic and hypolipidemic acitivity. Several of the compounds disclosed are novel per se.

  药物组合物含有式（I）的草酸衍生物作为活性成分： 其中 R 和 R2（可以相同或不同）各自代表氢或烷基或环烷基或基团 以及 R3 和 R4（可以相同或不同）各自代表氢、卤素、硝基或低级烷基或低级烷氧基，以及它们的药学上可接受的盐和金属络合物。这些组合物具有降血糖和降血脂活性。所公开的化合物中有几种本身就是新颖的。
• 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
• LIAO, ZENG-KUN;KOHN, H., J. ORG. CHEM., 1984, 49, N 25, 4745-4752
  作者：LIAO, ZENG-KUN、KOHN, H.

  DOI：——

  日期：——
• US4683240A
  申请人：——

  公开号：US4683240A

  公开（公告）日：1987-07-28
• 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.