2-((S)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl)isoindoline-1,3-dione | 877204-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((S)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl)isoindoline-1,3-dione
• 英文别名: 2-[(2S)-2-methyl-3-(oxan-2-yloxy)propyl]isoindole-1,3-dione
• CAS: 877204-14-3
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: WMSOPIDXISXQJS-SFVWDYPZSA-N

物化性质

• 沸点：
  447.6±40.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((S)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl)isoindoline-1,3-dione 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (-)-(S)-2-(3-hydroxy-2-methylpropyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship

  摘要：

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.

  DOI：

  10.1021/jm050756e
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-((S)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl)isoindoline-1,3-dione
  参考文献：
  名称：

  The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship

  摘要：

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.

  DOI：

  10.1021/jm050756e