BP-PM6 | 1175707-17-1

• 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: BP-PM6
• 英文别名: [[[4-[(E)-3-[[(2S,11S)-2-[[(2S)-5-amino-1-(benzylamino)-1,5-dioxopentan-2-yl]carbamoyl]-12-oxo-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-11-yl]amino]-3-oxoprop-1-enyl]phenyl]-difluoromethyl]-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
• CAS: 1175707-17-1
• 化学式: C₄₇H₅₆F₂N₅O₁₂P
• 分子量: 951.959
• InChiKey: GBOAAOCRBISTHG-WNKZAVQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  239
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  BP-PM6 在 水 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 ((((4-((E)-3-(((3S,6S)-6-(((S)-5-amino-1-(benzylamino)-1,5-dioxopentan-2-yl)carbamoyl)-4-oxo-1,2,3,4,6,7-hexahydroazepino[3,2,1-hi]indol-3-yl)amino)-3-oxoprop-1-en-1-yl)phenyl)difluoromethyl)(hydroxy)phosphoryl)oxy)methyl pivalate
  参考文献：
  名称：

  Synthesis of Phosphatase-Stable, Cell-Permeable Peptidomimetic Prodrugs That Target the SH2 Domain of Stat3

  摘要：

  The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.

  DOI：

  10.1021/ol9012662
• 作为产物：
  描述：

  pentachlorophenyl (E)-3-(4-(di(pivaloyloxymethyl)phosphoryldifluoromethyl)phenyl)prop-2-enoate 、 TFA *H-Haic-Gln-NHBn; Haic = 5-amino-1,2,4,5,6,7-hexahydro-4-oxoazepino[3,2,1-hi]indole-2-carboxylic acid 在 N-甲基吗啉 、 N-甲基吡咯烷酮 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到BP-PM6
  参考文献：
  名称：

  Synthesis of Phosphatase-Stable, Cell-Permeable Peptidomimetic Prodrugs That Target the SH2 Domain of Stat3

  摘要：

  The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.

  DOI：

  10.1021/ol9012662