((S)-1-Hydroxy-2-oxo-pyrrolidin-3-yl)-carbamic acid benzyl ester | 111772-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((S)-1-Hydroxy-2-oxo-pyrrolidin-3-yl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(3S)-1-hydroxy-2-oxopyrrolidin-3-yl]carbamate
• CAS: 111772-93-1
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: PZWSNZHWTMIWSJ-JTQLQIEISA-N

物化性质

• 熔点：
  173-174 °C
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.87
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((S)-1-Hydroxy-2-oxo-pyrrolidin-3-yl)-carbamic acid benzyl ester 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.17h， 以98%的产率得到(-)-3-氨基-1-羟基-2-吡咯酮
  参考文献：
  名称：

  4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase

  摘要：

  Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).

  DOI：

  10.1021/jm00397a037
• 作为产物：
  描述：

  (2S)-2-(benzyloxycarbonylamino)-4-hydroxybutyric acid benzyl ester 在 吡啶 、 盐酸羟胺 、 sodium cyanoborohydride 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 ((S)-1-Hydroxy-2-oxo-pyrrolidin-3-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase

  摘要：

  Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).

  DOI：

  10.1021/jm00397a037

文献信息

• FUSHIYA, SHINJI;MAEDA, KAZUTOSHI;FUNAYAMA, TOSHIHIKO;NOZOE, SHIGEO, J. MED. CHEM., 31,(1988) N 2, 480-483
  作者：FUSHIYA, SHINJI、MAEDA, KAZUTOSHI、FUNAYAMA, TOSHIHIKO、NOZOE, SHIGEO

  DOI：——

  日期：——
• 4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase
  作者：Shinji Fushiya、Kazutoshi Maeda、Toshihiko Funayama、Shigeo Nozoe

  DOI：10.1021/jm00397a037

  日期：1988.2

  Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).