N-(benzo[d][1,3]dioxol-5-yl(5-chloro-8-hydroxyquinolin-7-yl)methyl)butyramide

• 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: N-(benzo[d][1,3]dioxol-5-yl(5-chloro-8-hydroxyquinolin-7-yl)methyl)butyramide
• 英文别名: N-[Benzo[1,3]dioxol-5-yl-(5-chloro-8-hydroxy-quinolin-7-yl)-methyl]-butyramide；N-[1,3-benzodioxol-5-yl-(5-chloro-8-hydroxyquinolin-7-yl)methyl]butanamide
• 化学式: C₂₁H₁₉ClN₂O₄
• 分子量: 398.846
• InChiKey: BIQMEYCMAGHOEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(benzo[d][1,3]dioxol-5-yl(5-chloro-8-hydroxyquinolin-7-yl)methyl)butyramide 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以70%的产率得到N-(benzo[d][1,3]dioxol-5-yl(5-chloro-8-methoxyquinolin-7-yl)methyl)butyramide
  参考文献：
  名称：

  [EN] SMALL MOLECULE INHIBITORS OF GRP78 AND USES THEREOF
  [FR] INHIBITEURS À PETITES MOLÉCULES DE GRP78 ET LEURS UTILISATIONS

  摘要：

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules as defined within Formula I (as defined herein) which function as inhibitors of glucose-regulated protein 78 (GRP78) within cancer cells and/or immune cells, and which function as effective therapeutic agents for treating, ameliorating, and preventing various forms of cancer (e.g., pancreatic cancer), viral infections (e.g. SARS-CoV-2), and inflammatory diseases. In addition, this invention also relates to a new class of PROTACs having Formulas II, III and IV (as defined herein) which function as degraders of GRP78 within cancer and/or immune cells. Pharmaceutical compositions comprising said compounds of Formulas I, II, III, or IV are also within the scope of the present invention.

  公开号：

  WO2022169834A2
• 作为产物：
  描述：

  胡椒醛 、 丁酰胺 、 5-氯-8-羟基喹啉 以 neat (no solvent) 为溶剂， 以32%的产率得到N-(benzo[d][1,3]dioxol-5-yl(5-chloro-8-hydroxyquinolin-7-yl)methyl)butyramide
  参考文献：
  名称：

  [EN] SMALL MOLECULE INHIBITORS OF GRP78 AND USES THEREOF
  [FR] INHIBITEURS À PETITES MOLÉCULES DE GRP78 ET LEURS UTILISATIONS

  摘要：

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules as defined within Formula I (as defined herein) which function as inhibitors of glucose-regulated protein 78 (GRP78) within cancer cells and/or immune cells, and which function as effective therapeutic agents for treating, ameliorating, and preventing various forms of cancer (e.g., pancreatic cancer), viral infections (e.g. SARS-CoV-2), and inflammatory diseases. In addition, this invention also relates to a new class of PROTACs having Formulas II, III and IV (as defined herein) which function as degraders of GRP78 within cancer and/or immune cells. Pharmaceutical compositions comprising said compounds of Formulas I, II, III, or IV are also within the scope of the present invention.

  公开号：

  WO2022169834A2