H-Cha-bAla(2-OH,3S-Bom)-Gly-OEt | 1229293-88-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-Cha-bAla(2-OH,3S-Bom)-Gly-OEt
• 英文别名: ethyl 2-[[(3S)-3-[[(2S)-2-amino-3-cyclohexylpropanoyl]amino]-2-hydroxy-4-phenylmethoxybutanoyl]amino]acetate
• CAS: 1229293-88-2
• 化学式: C₂₄H₃₇N₃O₆
• 分子量: 463.574
• InChiKey: LIFNWQLQPFBTNV-ZDOMSUIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-硝基噻吩-2-甲酸 、 H-Cha-bAla(2-OH,3S-Bom)-Gly-OEt 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-[[(3S)-3-[[(2S)-3-cyclohexyl-2-[(5-nitrothiophene-2-carbonyl)amino]propanoyl]amino]-2-hydroxy-4-phenylmethoxybutanoyl]amino]acetate
  参考文献：
  名称：

  Design and Synthesis of α-Ketoamides as Cathepsin S Inhibitors with Potential Applications against Tumor Invasion and Angiogenesis

  摘要：

  A series of small molecules bearing an alpha-ketoamide warhead were synthesized and evaluated for their ability to inhibit cathepsin S, a key proteolytic enzyme upregulated in many cancers during tumor progression and metastasis. Most of the synthetic compounds were noncytotoxic, but several robustly inhibited cathepsin S (IC(50) < 10 nM) and potently suppressed cell migration, invasion, and capillary tube formation. These results highlight the potential of alpha-ketoamide therapy for preventing or delaying cancer spread.

  DOI：

  10.1021/jm100089e
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 H-Cha-bAla(2-OH,3S-Bom)-Gly-OEt
  参考文献：
  名称：

  Design and Synthesis of α-Ketoamides as Cathepsin S Inhibitors with Potential Applications against Tumor Invasion and Angiogenesis

  摘要：

  A series of small molecules bearing an alpha-ketoamide warhead were synthesized and evaluated for their ability to inhibit cathepsin S, a key proteolytic enzyme upregulated in many cancers during tumor progression and metastasis. Most of the synthetic compounds were noncytotoxic, but several robustly inhibited cathepsin S (IC(50) < 10 nM) and potently suppressed cell migration, invasion, and capillary tube formation. These results highlight the potential of alpha-ketoamide therapy for preventing or delaying cancer spread.

  DOI：

  10.1021/jm100089e