(2S)-3-phenyl-2-(pyridin-2-ylmethoxycarbonylamino)propanoic acid | 401917-92-8

• 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: (2S)-3-phenyl-2-(pyridin-2-ylmethoxycarbonylamino)propanoic acid
• CAS: 401917-92-8
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: MDMSCROWAATPPJ-AWEZNQCLSA-N

物化性质

• 沸点：
  523.5±50.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-巯基丙酸乙酯 、 ((S)-1-Benzyl-3-chloro-2-oxo-propyl)-carbamic acid allyl ester 、 (2S)-3-phenyl-2-(pyridin-2-ylmethoxycarbonylamino)propanoic acid 以65%的产率得到3-{2-Oxo-4-phenyl-3-[3-phenyl-2-(pyridin-2-ylmethoxycarbonylamino)-propionylamino]-butylsulfanyl}-propionic acid ethyl ester
  参考文献：
  名称：

  Identification of Potent and Selective Mechanism-Based Inhibitors of the Cysteine Protease Cruzain Using Solid-Phase Parallel Synthesis

  摘要：

  Targeted libraries of ketone-based cysteine protease inhibitors were synthesized and screened against cruzain, a cysteine protease implicated in Chagas' disease. A number of single digit nanomolar, low molecular weight inhibitors were identified and optimized for solubility and potency. Specifically, the best inhibitors identified have K-i values of 0.9-10 nM and molecular weights between 499 and 609 Da. The most effective inhibitor was also found to be greater than 1000-fold selective for cruzain relative to cathepsin B and 100-fold selective for cruzain relative to cathepsin L.

  DOI：

  10.1021/jm010333m
• 作为产物：
  描述：

  (S)-2-异氰酰基-3-苯基丙酸 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S)-3-phenyl-2-(pyridin-2-ylmethoxycarbonylamino)propanoic acid
  参考文献：
  名称：

  Identification of Potent and Selective Mechanism-Based Inhibitors of the Cysteine Protease Cruzain Using Solid-Phase Parallel Synthesis

  摘要：

  Targeted libraries of ketone-based cysteine protease inhibitors were synthesized and screened against cruzain, a cysteine protease implicated in Chagas' disease. A number of single digit nanomolar, low molecular weight inhibitors were identified and optimized for solubility and potency. Specifically, the best inhibitors identified have K-i values of 0.9-10 nM and molecular weights between 499 and 609 Da. The most effective inhibitor was also found to be greater than 1000-fold selective for cruzain relative to cathepsin B and 100-fold selective for cruzain relative to cathepsin L.

  DOI：

  10.1021/jm010333m