methyl (2S)-3-hydroxy-2-[(3-nitrophenyl)methylamino]propanoate | 179414-50-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-3-hydroxy-2-[(3-nitrophenyl)methylamino]propanoate
• CAS: 179414-50-7
• 化学式: C₁₁H₁₄N₂O₅
• 分子量: 254.243
• InChiKey: GCNIJQLVUGSYRV-JTQLQIEISA-N

物化性质

• 沸点：
  431.3±40.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-hydroxy-2-[(3-nitrophenyl)methylamino]propanoate 在 氢氧化钾 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 31.0h， 生成 1-(3-nitrobenzyl)-5-methylidene-2,4-dioxoimidazolidine-3-acetic acid
  参考文献：
  名称：

  Highly Selective Aldose Reductase Inhibitors. 3. Structural Diversity of 3-(Arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic Acids

  摘要：

  Accumulation of intracellular sorbitol, the reduced product of glucose, catalyzed by aldose reductase (AR) (EC 1.1.1.21), is thought to be the cause of the development of diabetic complications. Our attention is focused on finding compounds which inhibit AR without significantly inhibiting aldehyde reductase (ALR) (EC 1.1.1.2). The uracil or 2,4-dioxoimidazolidine skeleton having the benzothiazolyl or 4-chloro-3-nitrophenyl group as an aryl part indicated not only extremely high AR inhibitory activity but also AR selectivity. The ratio of IC50(ALR)/IC50(AR) of 3-[(5-chlorobenzothiazol-2-yl)methyl]-1,2,3,4-tetrahydro-2,4-dioxopyrim-idine-1-acetic acid (47d) was more than 17 500. The uracil skeleton with the benzothiazolyl moiety seemed to be the best combination for selective AR inhibition.

  DOI：

  10.1021/jm960594+
• 作为产物：
  描述：

  L-丝氨酸甲酯 、 间硝基苯甲醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以17%的产率得到methyl (2S)-3-hydroxy-2-[(3-nitrophenyl)methylamino]propanoate
  参考文献：
  名称：

  Highly Selective Aldose Reductase Inhibitors. 3. Structural Diversity of 3-(Arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic Acids

  摘要：

  Accumulation of intracellular sorbitol, the reduced product of glucose, catalyzed by aldose reductase (AR) (EC 1.1.1.21), is thought to be the cause of the development of diabetic complications. Our attention is focused on finding compounds which inhibit AR without significantly inhibiting aldehyde reductase (ALR) (EC 1.1.1.2). The uracil or 2,4-dioxoimidazolidine skeleton having the benzothiazolyl or 4-chloro-3-nitrophenyl group as an aryl part indicated not only extremely high AR inhibitory activity but also AR selectivity. The ratio of IC50(ALR)/IC50(AR) of 3-[(5-chlorobenzothiazol-2-yl)methyl]-1,2,3,4-tetrahydro-2,4-dioxopyrim-idine-1-acetic acid (47d) was more than 17 500. The uracil skeleton with the benzothiazolyl moiety seemed to be the best combination for selective AR inhibition.

  DOI：

  10.1021/jm960594+

文献信息

• Highly Selective Aldose Reductase Inhibitors. 3. Structural Diversity of 3-(Arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic Acids
  作者：Takayuki Kotani、Yasuhiro Nagaki、Akira Ishii、Yukari Konishi、Hisashi Yago、Seishi Suehiro、Nobuhisa Okukado、Kaoru Okamoto

  DOI：10.1021/jm960594+

  日期：1997.2.1

  Accumulation of intracellular sorbitol, the reduced product of glucose, catalyzed by aldose reductase (AR) (EC 1.1.1.21), is thought to be the cause of the development of diabetic complications. Our attention is focused on finding compounds which inhibit AR without significantly inhibiting aldehyde reductase (ALR) (EC 1.1.1.2). The uracil or 2,4-dioxoimidazolidine skeleton having the benzothiazolyl or 4-chloro-3-nitrophenyl group as an aryl part indicated not only extremely high AR inhibitory activity but also AR selectivity. The ratio of IC50(ALR)/IC50(AR) of 3-[(5-chlorobenzothiazol-2-yl)methyl]-1,2,3,4-tetrahydro-2,4-dioxopyrim-idine-1-acetic acid (47d) was more than 17 500. The uracil skeleton with the benzothiazolyl moiety seemed to be the best combination for selective AR inhibition.