ethyl 2-(6-(3-(3-(tert-butyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetate | 1192364-70-7

• 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: ethyl 2-(6-(3-(3-(tert-butyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetate
• CAS: 1192364-70-7
• 化学式: C₂₄H₃₀N₄O₆
• 分子量: 470.525
• InChiKey: PQSSITMSRWDVFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124.54
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(6-(3-(3-(tert-butyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetate 在 水 、 sodium hydroxide 、 柠檬酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以89%的产率得到2-(6-(3-(3-(tert-butyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetic acid
  参考文献：
  名称：

  Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA

  摘要：

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.

  DOI：

  10.1021/ol9019474
• 作为产物：
  描述：

  tert-butyl 3-(3-ethynylphenoxyl)propylcarbamate 、 ethyl (N⁴-benzoyl-5-iodocytosin-1-yl)acetate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙醇 为溶剂， 反应 36.0h， 以64%的产率得到ethyl 2-(6-(3-(3-(tert-butyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetate
  参考文献：
  名称：

  Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA

  摘要：

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.

  DOI：

  10.1021/ol9019474