perfluorophenyl (R)-4-(4-(4-(4-(4-amino-3-(((benzyloxy)carbonyl)amino)butanamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylate 2,2,2-trifluoroacetate | 1180012-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: perfluorophenyl (R)-4-(4-(4-(4-(4-amino-3-(((benzyloxy)carbonyl)amino)butanamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylate 2,2,2-trifluoroacetate
• CAS: 1180012-07-0
• 化学式: C₂HF₃O₂*C₄₁H₃₈F₅N₁₁O₈
• 分子量: 1021.84
• InChiKey: PNSGIOWYKUJSJN-ZMBIFBSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  72.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  276.96
• 氢给体数：
  7.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  perfluorophenyl (R)-4-(4-(4-(4-(4-amino-3-(((benzyloxy)carbonyl)amino)butanamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylate 2,2,2-trifluoroacetate 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以13.9%的产率得到cyclo-(-ImPyPyPy-(R)^β-NHCbzγ-ImPyPyPy-(R)^β-NHCbzγ-)
  参考文献：
  名称：

  Oligomerization Route to Py−Im Polyamide Macrocycles

  摘要：

  Cyclic eight-ring pyrrole-imidazole polyamides are sequence-specific DNA-binding small molecules that are cell permeable and can regulate endogenous gene expression. Syntheses of cyclic polyamides have been achieved by solid-phase and solution-phase methods. A rapid solution-phase oligomerization approach to eight-ring symmetrical cyclic polyamides yields 12- and 16-membered macrocycles as well. A preference for DNA binding by the 8- and 16-membered oligomers was observed over the 12-ring macrocycle, which we attributed to a conformational constraint not present in the smaller and larger systems.

  DOI：

  10.1021/ol901311m
• 作为产物：
  描述：

  (3R)-4-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-[[hydroxy(phenylmethoxy)methylidene]amino]-N-[1-methyl-2-[[1-methyl-5-[[1-methyl-5-[[1-methyl-5-(2,3,4,5,6-pentafluorophenoxy)carbonylpyrrol-3-yl]carbamoyl]pyrrol-3-yl]carbamoyl]pyrrol-3-yl]carbamoyl]imidazol-4-yl]butanimidic acid 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 perfluorophenyl (R)-4-(4-(4-(4-(4-amino-3-(((benzyloxy)carbonyl)amino)butanamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylate 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Oligomerization Route to Py−Im Polyamide Macrocycles

  摘要：

  Cyclic eight-ring pyrrole-imidazole polyamides are sequence-specific DNA-binding small molecules that are cell permeable and can regulate endogenous gene expression. Syntheses of cyclic polyamides have been achieved by solid-phase and solution-phase methods. A rapid solution-phase oligomerization approach to eight-ring symmetrical cyclic polyamides yields 12- and 16-membered macrocycles as well. A preference for DNA binding by the 8- and 16-membered oligomers was observed over the 12-ring macrocycle, which we attributed to a conformational constraint not present in the smaller and larger systems.

  DOI：

  10.1021/ol901311m