tert-butyl 2-(9-(3-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzyl)-9H-carbazol-2-yloxy)-acetate | 1204407-35-1

• 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: tert-butyl 2-(9-(3-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzyl)-9H-carbazol-2-yloxy)-acetate
• 英文别名: Tert-butyl 2-[9-[[3-[3-(trifluoromethyl)diazirin-3-yl]phenyl]methyl]carbazol-2-yl]oxyacetate
• CAS: 1204407-35-1
• 化学式: C₂₇H₂₄F₃N₃O₃
• 分子量: 495.501
• InChiKey: VGDQEGQQQYTVDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(9-(3-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzyl)-9H-carbazol-2-yloxy)-acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以76%的产率得到BSc3958
  参考文献：
  名称：

  NSAID-derived γ-secretase modulators. Part III: Membrane anchoring

  摘要：

  Selective lowering of A beta(42) levels with small-molecule substrate targeting c-secretase modulators (sGSMs), such as some non-steroidal anti-inflammatory drugs, is a promising therapeutic approach for Alzheimer's disease. Here we present N-substituted carbazole-and O-substituted fenofibrate-derived sGSMs and their activity data. Seven out of 19 screened compounds exhibited promising activity against A beta(42) secretion at a low micromolar level. We presume that the sGSMs interact with lys624 at the membrane interface and that the lipophilic substituents anchor the compound orientation in the membrane. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.035
• 作为产物：
  描述：

  tert-butyl 2-(9H-carbazol-2-yloxy)acetate 、 3-(3-(bromomethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以43%的产率得到tert-butyl 2-(9-(3-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzyl)-9H-carbazol-2-yloxy)-acetate
  参考文献：
  名称：

  NSAID-derived γ-secretase modulators. Part III: Membrane anchoring

  摘要：

  Selective lowering of A beta(42) levels with small-molecule substrate targeting c-secretase modulators (sGSMs), such as some non-steroidal anti-inflammatory drugs, is a promising therapeutic approach for Alzheimer's disease. Here we present N-substituted carbazole-and O-substituted fenofibrate-derived sGSMs and their activity data. Seven out of 19 screened compounds exhibited promising activity against A beta(42) secretion at a low micromolar level. We presume that the sGSMs interact with lys624 at the membrane interface and that the lipophilic substituents anchor the compound orientation in the membrane. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.035