1-(benzo[d][1,3]dioxol-5-ylmethyl)-5-benzyl-4-hydroxy-3-(9-octyl-9H-carbazol-2-yloxy)-1H-pyrrol-2(5H)-one | 1333215-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(benzo[d][1,3]dioxol-5-ylmethyl)-5-benzyl-4-hydroxy-3-(9-octyl-9H-carbazol-2-yloxy)-1H-pyrrol-2(5H)-one
• 英文别名: BSc 3966
• CAS: 1333215-50-1
• 化学式: C₃₉H₄₀N₂O₅
• 分子量: 616.757
• InChiKey: MUSBEUCLARNKFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.69
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.16
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (R)-methyl 2-(N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-(9-octyl-9H-carbazol-2-yloxy)acetamido)-3-phenylpropanoate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 以57%的产率得到1-(benzo[d][1,3]dioxol-5-ylmethyl)-5-benzyl-4-hydroxy-3-(9-octyl-9H-carbazol-2-yloxy)-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  NSAID-derived γ-secretase modulation requires an acidic moiety on the carbazole scaffold

  摘要：

  Modulation of gamma-secretase activity holds potential for the treatment of Alzheimer's disease. Most NSAID-derived gamma-secretase modulators feature a carboxylic acid, which may impair blood-brain barrier permeation. The structure activity relationship of 33 carbazoles featuring diverse carboxylic acid isosteres or metabolic precursors thereof was established in a cellular amyloid secretion assay. The modulatory activity was observed for acidic moieties and metabolically labile esters only, which supports our hypothesis of an acid-lysine interaction to be relevant for this type of gamma-secretase modulators. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.062