2-(6-(3-(2-(bis(tert-butyloxycarbonylamino)methyleneamino)ethoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetic acid | 1192364-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(6-(3-(2-(bis(tert-butyloxycarbonylamino)methyleneamino)ethoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetic acid
• CAS: 1192364-75-2
• 化学式: C₂₇H₃₄N₆O₈
• 分子量: 570.602
• InChiKey: ZNWJNDHBZFKFED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  186.23
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[2-((fluorenylmethoxycarbonyl)amino)ethyl]glycinate 、 2-(6-(3-(2-(bis(tert-butyloxycarbonylamino)methyleneamino)ethoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 以76%的产率得到benzyl N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[2-(6-(3-(2-(bis(tert-butyloxycarbonylamino)methyleneamino)ethoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetyl]glycinate
  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：

  ethyl 2-(6-(3-(2-(bis(tert-butyloxycarbonylamino)methyleneamino)ethoxy)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-(2-(bis(tert-butyloxycarbonylamino)methyleneamino)ethoxy)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