tert-butyl 2-(9H-carbazol-2-yloxy)acetate | 210410-32-5

• 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-(9H-carbazol-2-yloxy)acetate
• CAS: 210410-32-5
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: MPVCXBGATRZOGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(9H-carbazol-2-yloxy)acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (9H-carbazol)-2-yloxyacetic acid
  参考文献：
  名称：

  N-Substituted carbazolyloxyacetic acids modulate Alzheimer associated γ-secretase

  摘要：

  N-Sulfonylated and N-alkylated carbazolyloxyacetic acids were investigated for the inhibition and modulation of the Alzheimer's disease associated gamma-secretase. The introduction of a lipophilic substituent, which may vary from arylsulfone to alkyl, turned 2-carbazolyloxyacetic acids into potent gamma-secretase modulators. This resulted in the selective reduction of A beta(42) and an increase of the less aggregatory A beta(38) fragment by several compounds (e.g., 7d and 8c). Introduction of an electron donating group at position 6 and 8 of N-substituted carbazolyloxyacetic acids either decreased the activity or inversed modulation. The most active compounds displayed activity on amyloid precursor protein (APP) overexpressing cell lines in the low micromolar range and little or no effect on the gamma-secretase cleavage at the F-site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.061
• 作为产物：
  描述：

  2-羟基咔唑 、 氯乙酸叔丁酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.5h， 以99%的产率得到tert-butyl 2-(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