allyl (3-(7-hydroxy-2-oxo-2H-chromen-4-yl)propyl)carbamate | 1607803-62-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: allyl (3-(7-hydroxy-2-oxo-2H-chromen-4-yl)propyl)carbamate
• CAS: 1607803-62-2
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: QMWIIDNMPIEGTH-UHFFFAOYSA-N

物化性质

• 沸点：
  536.8±50.0 °C(predicted)
• 密度：
  1.258±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.77
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  乌洛托品 、 allyl (3-(7-hydroxy-2-oxo-2H-chromen-4-yl)propyl)carbamate 在 溶剂黄146 作用下， 反应 20.0h， 以18%的产率得到allyl-8-formyl-9-hydroxy-6-oxo-2,3,5, 6-tetrahydrochromeno[3,4-c]azepine-4(1H)-carboxylate
  参考文献：
  名称：

  Synthesis of Novel Tricyclic Chromenone-Based Inhibitors of IRE-1 RNase Activity

  摘要：

  Inositol-requiring enzyme 1 (IRE-1) is a kinase/RNase ER stress sensor that is activated in response to excessive accumulation of unfolded proteins, hypoxic conditions, calcium imbalance, and other stress stimuli. Activation of IRE-1 RNase function exerts a cytoprotective effect and has been implicated in the progression of cancer via increased expression of the transcription factor XBP-1s. Here, we describe the synthesis and biological evaluation of novel chromenone-based covalent inhibitors of IRE-1. Preparation of a family of 8-formyltetrahydrochromeno[3,4-c]pyridines was achieved via a Duff formylation that is attended by an unusual cyclization reaction. Biological evaluation in vitro and in whole cells led to the identification of 30 as a potent inhibitor of IRE-1 RNase activity and XBP-1s expression in wild type B cells and human mantle cell lymphoma cell lines.

  DOI：

  10.1021/jm5002452
• 作为产物：
  描述：

  4-(allyloxycarbonyl)aminobutanoic acid 在 4-二甲氨基吡啶 、 甲烷磺酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲烷磺酸 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 allyl (3-(7-hydroxy-2-oxo-2H-chromen-4-yl)propyl)carbamate
  参考文献：
  名称：

  Synthesis of Novel Tricyclic Chromenone-Based Inhibitors of IRE-1 RNase Activity

  摘要：

  Inositol-requiring enzyme 1 (IRE-1) is a kinase/RNase ER stress sensor that is activated in response to excessive accumulation of unfolded proteins, hypoxic conditions, calcium imbalance, and other stress stimuli. Activation of IRE-1 RNase function exerts a cytoprotective effect and has been implicated in the progression of cancer via increased expression of the transcription factor XBP-1s. Here, we describe the synthesis and biological evaluation of novel chromenone-based covalent inhibitors of IRE-1. Preparation of a family of 8-formyltetrahydrochromeno[3,4-c]pyridines was achieved via a Duff formylation that is attended by an unusual cyclization reaction. Biological evaluation in vitro and in whole cells led to the identification of 30 as a potent inhibitor of IRE-1 RNase activity and XBP-1s expression in wild type B cells and human mantle cell lymphoma cell lines.

  DOI：

  10.1021/jm5002452