天然氨基酸极其衍生物 | 199118-68-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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
• 中文名称: 天然氨基酸极其衍生物
• 中文别名: (3S)-3,4-二氨基-4-氧代丁酸苄酯单盐酸盐；4-苄酯-L-天冬氨酰胺盐酸盐
• 英文名称: H-Asp(OBzl)-CONH₂ hydrochloride
• 英文别名: H-Asp(obzl)-NH2 hcl；benzyl (3S)-3,4-diamino-4-oxobutanoate;hydrochloride
• CAS: 199118-68-8
• 化学式: C₁₁H₁₄N₂O₃*ClH
• 分子量: 258.705
• InChiKey: STBSUQZEDYTKDV-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  天然氨基酸极其衍生物 、 在 lithium hydroxide 、 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以68%的产率得到
  参考文献：
  名称：

  Flat SAR of P3-methylsulphonamide based small molecule legumain inhibitors

  摘要：

  This letter describes the design, development and SAR exploration of a novel series of small legumain inhibitors. The SAR of a new small molecule legumain inhibitor chemotype was explored and found to have improved physiochemical properties compared to previously developed inhibitors within our group. However, further development of this series was found to be limited as the SAR was observed to be relatively flat. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.101

文献信息

• Identification and SAR exploration of a novel series of Legumain inhibitors
  作者：Sharon L. Eddie、Aaron Gregson、Emma Graham、Stephanie Burton、Timothy Harrison、Roberta Burden、Christopher J. Scott、Paul B. Mullan、Rich Williams

  DOI：10.1016/j.bmcl.2019.03.019

  日期：2019.6

  This letter describes the development of a series of potent and selective small molecule Legumain inhibitors suitable as chemical probes for in vitro experiments. Our previous research had identified a dipeptide inhibitor utilizing a semi-reversible cyano warhead that generated 2, a cell active inhibitor. This work explores an alternative P2-P3 linker and further SAR exploration of the P3 group which

  这封信描述了一系列有效的和选择性的小分子Legumain抑制剂的开发，这些抑制剂适合用作体外实验的化学探针。我们之前的研究已经确定了一种利用半可逆的氰基战斗部产生的二肽抑制剂，该头可产生2种细胞活性抑制剂。这项工作探索了另一种P2-P3连接子，并进一步探索了P3基团的SAR，从而鉴定了16i，这是一种具有出色的理化特性的高效抑制剂。
• 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.
• Flat SAR of P3-methylsulphonamide based small molecule legumain inhibitors
  作者：Kerry Anne Ness、Sharon L. Eddie、Stephanie Burton、Timothy Harrison、Paul Mullan、Rich Williams

  DOI：10.1016/j.bmcl.2015.11.101

  日期：2016.1

  This letter describes the design, development and SAR exploration of a novel series of small legumain inhibitors. The SAR of a new small molecule legumain inhibitor chemotype was explored and found to have improved physiochemical properties compared to previously developed inhibitors within our group. However, further development of this series was found to be limited as the SAR was observed to be relatively flat. (C) 2015 Elsevier Ltd. All rights reserved.