(S)-4-bromobenzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate | 1609689-78-2

• 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: (S)-4-bromobenzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate
• 英文别名: (4-bromophenyl)methyl (2S)-2-[[(1S)-3-amino-1-cyano-3-oxopropyl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 1609689-78-2
• 化学式: C₁₇H₁₉BrN₄O₄
• 分子量: 423.266
• InChiKey: IBPXYGJUPZPJQF-KBPBESRZSA-N

物化性质

• 沸点：
  722.349±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.520±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-bromobenzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate 、 2-氯-5-吡啶硼酸 在 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-(6-chloropyridin-3-yl)benzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  P3 SAR exploration of biphenyl carbamate based Legumain inhibitors

  摘要：

  This Letter describes the further development and SAR exploration of a novel series of Legumain inhibitors. Based upon a previously identified Legumain inhibitor from our group, we explored the SAR of the carbamate phenyl ring system to probe the P3 pocket of the enzyme. This led to the identification of a sub-nanomolar inhibitor of Legumain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.002
• 作为产物：
  描述：

  (4-溴苯基)甲基(4-硝基苯基)碳酸酯 在 N-甲基吗啉 、 三聚氯氰 、 水 、 氯化铵 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.0h， 生成 (S)-4-bromobenzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  P3 SAR exploration of biphenyl carbamate based Legumain inhibitors

  摘要：

  This Letter describes the further development and SAR exploration of a novel series of Legumain inhibitors. Based upon a previously identified Legumain inhibitor from our group, we explored the SAR of the carbamate phenyl ring system to probe the P3 pocket of the enzyme. This led to the identification of a sub-nanomolar inhibitor of Legumain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.002

文献信息

• P3 SAR exploration of biphenyl carbamate based Legumain inhibitors
  作者：Catherine Higgins、Samira Bouazzaoui、Kishore Gaddale、Zenobia D’Costa、Amy Templeman、Martin O’Rourke、Andrew Young、Christopher Scott、Tim Harrison、Paul Mullan、Rich Williams

  DOI：10.1016/j.bmcl.2014.04.002

  日期：2014.6

  This Letter describes the further development and SAR exploration of a novel series of Legumain inhibitors. Based upon a previously identified Legumain inhibitor from our group, we explored the SAR of the carbamate phenyl ring system to probe the P3 pocket of the enzyme. This led to the identification of a sub-nanomolar inhibitor of Legumain. (C) 2014 Elsevier Ltd. All rights reserved.