[(S)-1-((S)-1-Benzyl-3-bromo-2-oxo-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester | 118252-76-9

• 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)-1-((S)-1-Benzyl-3-bromo-2-oxo-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[[(2S)-4-bromo-3-oxo-1-phenylbutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 118252-76-9
• 化学式: C₂₄H₂₉BrN₂O₄
• 分子量: 489.409
• InChiKey: UUZLPPYAVBFCMG-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-1-((S)-1-Benzyl-3-bromo-2-oxo-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(S)-1-((S)-1-Benzyl-3-fluoro-2-oxo-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Calpain inhibitors based on the quiescent affinity label concept: high rates of calpain inactivation with leaving groups derived from N-hydroxy peptide coupling reagents

  摘要：

  A series of irreversible inhibitors of recombinant calpain has been synthesized and their rates of inactivation have been evaluated against calpain and cathepsin B, respectively. The design of the inhibitors was based on the quiescent affinity label concept. By choosing the appropriate affinity group and by employing leaving groups derived from N-hydroxy coupling reagents, good inhibitors of calpain with high rates of inactivation have been identified. However, poor aqueous stability limits their therapeutic utility. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00451-0
• 作为产物：
  描述：

  苄氧羰基-亮氨酰-苯丙氨酸 在 N-甲基吗啉 、 氢溴酸 、 氯甲酸异丁酯 作用下， 以 溶剂黄146 为溶剂， 生成 [(S)-1-((S)-1-Benzyl-3-bromo-2-oxo-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Calpain inhibitors based on the quiescent affinity label concept: high rates of calpain inactivation with leaving groups derived from N-hydroxy peptide coupling reagents

  摘要：

  A series of irreversible inhibitors of recombinant calpain has been synthesized and their rates of inactivation have been evaluated against calpain and cathepsin B, respectively. The design of the inhibitors was based on the quiescent affinity label concept. By choosing the appropriate affinity group and by employing leaving groups derived from N-hydroxy coupling reagents, good inhibitors of calpain with high rates of inactivation have been identified. However, poor aqueous stability limits their therapeutic utility. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00451-0

文献信息

• Aspartyl .alpha.-((Diphenylphosphinyl)oxy)methyl Ketones as Novel Inhibitors of Interleukin-1.beta. Converting Enzyme. Utility of the Diphenylphosphinic Acid Leaving Group for the Inhibition of Cysteine Proteases
  作者：Roland E. Dolle、Jasbir Singh、David Whipple、I. Kelly Osifo、Gary Speier、Todd L. Graybill、Jill S. Gregory、Alex L. Harris、Carla T. Helaszek

  DOI：10.1021/jm00002a002

  日期：1995.1
• Calpain inhibitors based on the quiescent affinity label concept: high rates of calpain inactivation with leaving groups derived from N-hydroxy peptide coupling reagents
  作者：Rabindranath Tripathy、Mark A. Ator、John P. Mallamo

  DOI：10.1016/s0960-894x(00)00451-0

  日期：2000.10

  A series of irreversible inhibitors of recombinant calpain has been synthesized and their rates of inactivation have been evaluated against calpain and cathepsin B, respectively. The design of the inhibitors was based on the quiescent affinity label concept. By choosing the appropriate affinity group and by employing leaving groups derived from N-hydroxy coupling reagents, good inhibitors of calpain with high rates of inactivation have been identified. However, poor aqueous stability limits their therapeutic utility. (C) 2000 Elsevier Science Ltd. All rights reserved.