1-Methoxy-7-[(4-methoxyphenyl)methoxy]-9H-carbazole | 920982-67-8

• 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-Methoxy-7-[(4-methoxyphenyl)methoxy]-9H-carbazole
• 英文别名: 1-methoxy-7-[(4-methoxyphenyl)methoxy]-9H-carbazole
• CAS: 920982-67-8
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: ULNRUJSUSVNTLC-UHFFFAOYSA-N

物化性质

• 沸点：
  551.5±40.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methoxy-7-[(4-methoxyphenyl)methoxy]-9H-carbazole 在 palladium on activated charcoal 氢气 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 14.0h， 生成 2-[8-methoxy-9-(4-phenylphenyl)sulfonylcarbazol-2-yl]oxyacetic 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：

  4-氯-3-硝基苯酚 在 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 作用下， 以 水 、 邻二氯苯 、 丙酮 、 甲苯 为溶剂， 反应 32.0h， 生成 1-Methoxy-7-[(4-methoxyphenyl)methoxy]-9H-carbazole
  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

文献信息

• N-Substituted carbazolyloxyacetic acids modulate Alzheimer associated γ-secretase
  作者：Rajeshwar Narlawar、Blanca I. Pérez Revuelta、Karlheinz Baumann、Robert Schubenel、Christian Haass、Harald Steiner、Boris Schmidt

  DOI：10.1016/j.bmcl.2006.09.061

  日期：2007.1

  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.