2-(3-hydroxyphenanthridin-6-yl)-isoindole-1,3-dione | 1207463-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(3-hydroxyphenanthridin-6-yl)-isoindole-1,3-dione
• CAS: 1207463-33-9
• 化学式: C₂₁H₁₂N₂O₃
• 分子量: 340.338
• InChiKey: XPWNKBRELNYFSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.5
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(6-benzyloxycarbonylaminohexanoylamino)pentan-1-ol 、 2-(3-hydroxyphenanthridin-6-yl)-isoindole-1,3-dione 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到(5-(5-[6-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-phenanthridin-3-yloxy]-pentylcarbamoyl)-pentyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Conjugates of 6-Aminophenanthridine and Guanabenz, Two Structurally Unrelated Prion Inhibitors, for the Determination of Their Cellular Targets by Affinity Chromatography

  摘要：

  The synthesis of affinity matrices for 6-aminophenanthridine (6AP) and 2,6-dichlorobenzylidenaminoguanidine (Guanabenz, GA), two unrelated prion inhibitors, is described. In both cases, the same simple spacer, epsilon-aminocaproylaminopentanol, was introduced by a Mitsunobu reaction and the choice of the anchoring position of the linker was determined by the study of the residual antiprion activity of the corresponding 6AP or GA conjugates. Very recently, these two affinity matrices were used for chromatography assays leading to the identification of ribosome (via the rRNA) as a common target of these two antiprion drugs. Here, we show, using competition experiments with Quinacrine (QC) and Chlorpromazine (CPZ), two other antiprion drugs, that QC, but not CPZ, may also directly target the rRNA.

  DOI：

  10.1021/bc900314n
• 作为产物：
  描述：

  2-(3-benzyloxyphenanthridin-6-yl)-isoindole-1,3-dione 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以98%的产率得到2-(3-hydroxyphenanthridin-6-yl)-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of Conjugates of 6-Aminophenanthridine and Guanabenz, Two Structurally Unrelated Prion Inhibitors, for the Determination of Their Cellular Targets by Affinity Chromatography

  摘要：

  The synthesis of affinity matrices for 6-aminophenanthridine (6AP) and 2,6-dichlorobenzylidenaminoguanidine (Guanabenz, GA), two unrelated prion inhibitors, is described. In both cases, the same simple spacer, epsilon-aminocaproylaminopentanol, was introduced by a Mitsunobu reaction and the choice of the anchoring position of the linker was determined by the study of the residual antiprion activity of the corresponding 6AP or GA conjugates. Very recently, these two affinity matrices were used for chromatography assays leading to the identification of ribosome (via the rRNA) as a common target of these two antiprion drugs. Here, we show, using competition experiments with Quinacrine (QC) and Chlorpromazine (CPZ), two other antiprion drugs, that QC, but not CPZ, may also directly target the rRNA.

  DOI：

  10.1021/bc900314n