(S)-N-(4-(hydroxymethyl)phenyl)-2-((S)-3-methyl-2-(tritylamino)butanamido)-5-ureidopentanamide | 1022094-29-6

• 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)-N-(4-(hydroxymethyl)phenyl)-2-((S)-3-methyl-2-(tritylamino)butanamido)-5-ureidopentanamide
• CAS: 1022094-29-6
• 化学式: C₃₇H₄₃N₅O₄
• 分子量: 621.78
• InChiKey: JGJAZEJSQPGSHI-LQJZCPKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  145.58
• 氢给体数：
  6.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-(hydroxymethyl)phenyl)-2-((S)-3-methyl-2-(tritylamino)butanamido)-5-ureidopentanamide 、 二(对硝基苯)碳酸酯 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 18.0h， 以79%的产率得到4-((S)-2-((S)-3-methyl-2-(tritylamino)butanamido)-5-ureidopentanamido)benzyl (4-nitrophenyl) carbonate
  参考文献：
  名称：

  A cell-penetrating peptidic GRP78 ligand for tumor cell-specific prodrug therapy

  摘要：

  Tumor targeting peptides are promising vehicles for site-directed cancer therapy. Pep42, a cyclic 13-mer oligopeptide that specifically binds to glucose-regulated protein 78 (GRP78) and internalized into cancer cells, represents an excellent vehicle for tumor cell-specific chemotherapy. Here, we report the synthesis and evaluation of Pep42-prodrug conjugates that contain a cathepsin B-cleavable linker, resulting in the traceless release of drug inside the cancer cells. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.060
• 作为产物：
  描述：

  Val-cit-PAB-OH（VAL-CIT-PAB-羟基） 、 三苯基甲基溴 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以43%的产率得到(S)-N-(4-(hydroxymethyl)phenyl)-2-((S)-3-methyl-2-(tritylamino)butanamido)-5-ureidopentanamide
  参考文献：
  名称：

  A cell-penetrating peptidic GRP78 ligand for tumor cell-specific prodrug therapy

  摘要：

  Tumor targeting peptides are promising vehicles for site-directed cancer therapy. Pep42, a cyclic 13-mer oligopeptide that specifically binds to glucose-regulated protein 78 (GRP78) and internalized into cancer cells, represents an excellent vehicle for tumor cell-specific chemotherapy. Here, we report the synthesis and evaluation of Pep42-prodrug conjugates that contain a cathepsin B-cleavable linker, resulting in the traceless release of drug inside the cancer cells. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.060