Z-D-Ala-Phe-Lys(Z)-OH | 294173-01-6

• 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: Z-D-Ala-Phe-Lys(Z)-OH
• 英文别名: Cbz-D-Ala-Phe-Lys(Cbz)(Cbz)-OH；(2S)-6-(phenylmethoxycarbonylamino)-2-[[(2S)-3-phenyl-2-[[(2R)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]amino]hexanoic acid
• CAS: 294173-01-6
• 化学式: C₃₄H₄₀N₄O₈
• 分子量: 632.714
• InChiKey: MIRLPAKWKDFEKE-MHZHKKNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Z-D-Ala-Phe-Lys(Z)-OH 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 Z-D-Ala-Phe-Lys(Z)-N(Me)-(CH2)2-N(Me)-Boc
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2‘-Carbamate-Linked and 2‘-Carbonate-Linked Prodrugs of Paclitaxel:  Selective Activation by the Tumor-Associated Protease Plasmin

  摘要：

  The nontoxic paclitaxel-2'-carbamate prodrugs 2-5 and paclitaxel-2'-carbonate prodrug 6 were synthesized and tested for activation by the tumor-associated enzyme plasmin. A generally applicable method for the synthesis of paditaxel-2'-carbamates was developed. In buffer solution, prodrug 2, which contained an unsubstituted ethylenediamine spacer, was not stable, whereas prodrugs 3-6 were highly stable. Prodrugs 3-6 showed on average a decrease in cytotoxicity of more than 8000-fold in comparison with the parent drug in seven human tumor cell lines. Prodrugs 5 and 6 are the most nontoxic prodrugs of paclitaxel that yield the free parent drug upon selective activation currently reported. Enzyme hydrolysis and spacer elimination rates were determined by incubation of prodrugs 5 and 6 in the presence of human plasmin. From these results, prodrug 6 was selected as the promising prodrug for further in vivo studies.

  DOI：

  10.1021/jm0009078
• 作为产物：
  描述：

  以 甲醇 为溶剂， 生成 Z-D-Ala-Phe-Lys(Z)-OH
  参考文献：
  名称：

  Markowska, Agnieszka; Midura-Nowaczek, Krystyna; Bruzgo, Irena, Acta poloniae pharmaceutica, 2007, vol. 64, # 4, p. 355 - 358

  摘要：

  DOI：