2-acetylamino-2-<2-(2-amino-phenyl)-2-oxo-ethyl>-malonic acid diethyl ester | 175657-72-4

• 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: 2-acetylamino-2-<2-(2-amino-phenyl)-2-oxo-ethyl>-malonic acid diethyl ester
• 英文别名: Diethyl 2-acetamido-2-[2-(2-aminophenyl)-2-oxoethyl]propanedioate
• CAS: 175657-72-4
• 化学式: C₁₇H₂₂N₂O₆
• 分子量: 350.371
• InChiKey: XEHUZZKTUQYTIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  582.5±50.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-acetylamino-2-<2-(2-amino-phenyl)-2-oxo-ethyl>-malonic acid diethyl ester 在 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Derivatives of kynurenine as inhibitors of rat brain kynurenine aminotransferase

  摘要：

  The structural requirements of the catalytic site of kynurenine aminotransferase (KAT), the enzyme responsible for the conversion of L-kynurenine (KYN) to kynurenic acid (KYNA), were examined using analogs and derivatives of KYN: KYNA production from KYN was monitored in rat brain homogenates and brain tissue slices. Modification of KYN's acylalanine side chain or its ring amino group resulted in compounds which did not substantially affect KYNA synthesis. Ring chlorination in positions 3, 4, 5 and 6 yielded KYN analogs which interfered with KYNA production. L-5-Cl-KYN was the most active of the chlorinated kynurenines, and one of the most potent of several other 5-substituted kynurenines. L-5-Cl-KYN was an excellent substrate of KAT, yielding 6-Cl-KYNA. Finally, in kinetic studies, L-5-Cl-KYN (K-i = 5.4 mu M) was found to have an approximately five times higher affinity to the enzyme than the natural substrate KYN (K-m = 28 mu M).

  DOI：

  10.1016/s0223-5234(96)80002-x
• 作为产物：
  描述：

  1-(2-氨苯基)-2-氯乙酮 、 乙酰氨基丙二酸二乙酯 在 sodium 作用下， 生成 2-acetylamino-2-<2-(2-amino-phenyl)-2-oxo-ethyl>-malonic acid diethyl ester
  参考文献：
  名称：

  Derivatives of kynurenine as inhibitors of rat brain kynurenine aminotransferase

  摘要：

  The structural requirements of the catalytic site of kynurenine aminotransferase (KAT), the enzyme responsible for the conversion of L-kynurenine (KYN) to kynurenic acid (KYNA), were examined using analogs and derivatives of KYN: KYNA production from KYN was monitored in rat brain homogenates and brain tissue slices. Modification of KYN's acylalanine side chain or its ring amino group resulted in compounds which did not substantially affect KYNA synthesis. Ring chlorination in positions 3, 4, 5 and 6 yielded KYN analogs which interfered with KYNA production. L-5-Cl-KYN was the most active of the chlorinated kynurenines, and one of the most potent of several other 5-substituted kynurenines. L-5-Cl-KYN was an excellent substrate of KAT, yielding 6-Cl-KYNA. Finally, in kinetic studies, L-5-Cl-KYN (K-i = 5.4 mu M) was found to have an approximately five times higher affinity to the enzyme than the natural substrate KYN (K-m = 28 mu M).

  DOI：

  10.1016/s0223-5234(96)80002-x

文献信息

• [EN] METHODS FOR THE SYNTHESIS OF CHIRAL KYNURENINE COMPOUNDS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE COMPOSÉS DE KYNURÉNINE CHIRAUX
  申请人：VISTAGEN THERAPEUTICS INC

  公开号：WO2014152752A1

  公开（公告）日：2014-09-25

  Provided are methods for synthesizing compounds, including chiral kynurenine compounds. The methods are suitable for large-scale manufacture and produce the chiral kynurenines compounds in high chemical purity and high chiral purity.

  提供了合成化合物的方法，包括手性的骈氨酸化合物。这些方法适用于大规模生产，并且能够以高化学纯度和高手性纯度生产手性的骈氨酸化合物。
• METHODS FOR THE SYNTHESIS OF CHIRAL KYNURENINE COMPOUNDS
  申请人：VISTAGEN THERAPEUTICS, INC.

  公开号：US20160032334A1

  公开（公告）日：2016-02-04

  Provided are methods for synthesizing compounds, including chiral kynurenine compounds. The methods are suitable for large-scale manufacture and produce the chiral kynurenines compounds in high chemical purity and high chiral purity.

  提供了一种合成化合物的方法，包括手性的犬尿氨酸化合物。该方法适用于大规模生产，并能以高化学纯度和高手性纯度生产手性犬尿氨酸化合物。
• Methods for the synthesis of chiral kynurenine compounds
  申请人：VISTAGEN THERAPEUTICS, INC.

  公开号：US10294502B2

  公开（公告）日：2019-05-21

  Provided are methods for synthesizing compounds, including chiral kynurenine compounds. The methods are suitable for large-scale manufacture and produce the chiral kynurenines compounds in high chemical purity and high chiral purity.

  本文提供了合成化合物（包括手性犬尿氨酸化合物）的方法。这些方法适用于大规模生产，并能生产出高化学纯度和高手性纯度的手性犬尿氨酸化合物。
• US9834801B2
  申请人：——

  公开号：US9834801B2

  公开（公告）日：2017-12-05