Z-(7-bromo)Trp(Boc)-OtBu | 911675-17-7

• 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: Z-(7-bromo)Trp(Boc)-OtBu
• CAS: 911675-17-7
• 化学式: C₂₈H₃₃BrN₂O₆
• 分子量: 573.484
• InChiKey: YTSBXOMHMQEAMR-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  95.86
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Z-(7-bromo)Trp(Boc)-OtBu 在 盐酸 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 2.83h， 生成 Z-(7-bromo)Trp-NHMe
  参考文献：
  名称：

  Linear TMC-95-Based Proteasome Inhibitors

  摘要：

  We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and termini greatly influenced both the efficiency and selectivity of action on a given type of active site. Inhibition constants were submicromolar (K-i approximate to 300 nM) despite the absence of the entropically favorable constrained conformation that is characteristic of TMC-95A and its cyclic analogues. These linear compounds were readily prepared and reasonably stable in culture medium and could be optimized to inhibit one, two, or all three proteasome catalytic sites. Cytotoxicity assays performed on a series of human tumor cell lines identified the most potent inhibitors in cells.

  DOI：

  10.1021/jm0701324
• 作为产物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 、 (7-bromo)Trp(Boc)-OtBu 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以96%的产率得到Z-(7-bromo)Trp(Boc)-OtBu
  参考文献：
  名称：

  Linear TMC-95-Based Proteasome Inhibitors

  摘要：

  We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and termini greatly influenced both the efficiency and selectivity of action on a given type of active site. Inhibition constants were submicromolar (K-i approximate to 300 nM) despite the absence of the entropically favorable constrained conformation that is characteristic of TMC-95A and its cyclic analogues. These linear compounds were readily prepared and reasonably stable in culture medium and could be optimized to inhibit one, two, or all three proteasome catalytic sites. Cytotoxicity assays performed on a series of human tumor cell lines identified the most potent inhibitors in cells.

  DOI：

  10.1021/jm0701324

文献信息

• WO2006/105811
  申请人：——

  公开号：——

  公开（公告）日：——