9-n-octyl-2-hydroxycarbazole

• 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: 9-n-octyl-2-hydroxycarbazole
• 英文别名: BSc4029；2-hydroxy-N-octylcarbazole；9-Octylcarbazol-2-ol
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: YKLDNHOPFKEADH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-n-octyl-2-hydroxycarbazole 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 32.5h， 生成 BSc3986
  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
• 作为产物：
  描述：

  2-羟基咔唑 、 1-溴辛烷 在 sodium hydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以74%的产率得到9-n-octyl-2-hydroxycarbazole
  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

文献信息

• Conjugated poly(2,7-carbazole) derivatives and process for the preparation thereof
  申请人：——

  公开号：US20030092880A1

  公开（公告）日：2003-05-15

  The invention relates to conjugated poly(2,7-carbazole) derivatives comprising repeating, alternating or random units of the formula: 1 wherein R represents a linear or branched alkyl group having 1 to 22 carbon atoms. The conjugated poly(2,7-carbazole) derivatives according to the invention have interesting optical and electrochemical properties which render them suitable for use in the manufacture of diverse electrical, optical and electro-optical devices.

  本发明涉及共轭聚合物（2,7-咔唑）衍生物，包含公式1中的重复、交替或随机单元，其中R代表具有1至22个碳原子的线性或支链烷基。根据本发明，共轭聚合物（2,7-咔唑）衍生物具有有趣的光学和电化学性质，使其适用于制造各种电气、光学和电光设备。
• Conjugated polycarbazole derivatives and process for the preparation thereof
  申请人：——

  公开号：US20020103332A1

  公开（公告）日：2002-08-01

  The invention relates to conjugated polycarbazole derivates comprising repeating or alternating units of the formula: 1 wherein R represents a linear or branched alkyl group having 1 to 22 carbon atoms. The conjugated polycarbazole derivatives according to the invention have interesting optical and electrochemical properties which render them suitable for use in the manufacture of diverse electrical, optical and electro-optical devices.

  该发明涉及共轭聚合物咔唑衍生物，包括公式1的重复或交替单元，其中R代表具有1至22个碳原子的线性或支链烷基。根据本发明的共轭聚合物咔唑衍生物具有有趣的光学和电化学性质，使它们适用于制造各种电气、光学和电光学设备。
• Chemoselective N-alkylation of 2-hydroxycarbazole as a model for the synthesis of N-substituted pyrrole derivatives containing acidic functions
  作者：Domenico Albanese、Dario Landini、Michele Penso、Giovanni Spanò、Artan Trebicka

  DOI：10.1016/0040-4020(95)00232-w

  日期：1995.5

  2-Hydroxycarbazole (1) was chemoselectively N-alkylated with several alkyl halides 3 by generating the corresponding N,O-dianion using excess sodium hydride in a suitable solvent, under anhydrous conditions. The highest yields (87-96%) of 9-alkyl-2-hydroxycarbazoles 4 and the mildest reaction conditions were reached in THF containing DMF as an additive (2 mol equiv), but other solvents (DMSO, diglyme, DME) or solvent-additive systems (THF-diglyme, THF-DMSO, DME-DMF, diglyme-DMF) are effective.
• US6833432B2
  申请人：——

  公开号：US6833432B2

  公开（公告）日：2004-12-21
• NSAID-derived γ-secretase modulation requires an acidic moiety on the carbazole scaffold
  作者：Andrea Zall、Daniel Kieser、Nicole Höttecke、Eva C. Naumann、Binia Thomaszewski、Katrin Schneider、Dirk T. Steinbacher、Robert Schubenel、Stefan Masur、Karlheinz Baumann、Boris Schmidt

  DOI：10.1016/j.bmc.2011.06.062

  日期：2011.8

  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.