BSc3018 | 918547-84-9

• 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: BSc3018
• 英文别名: Benzyl 2-(6-chloro-9-octylcarbazol-2-yl)propanoate
• CAS: 918547-84-9
• 化学式: C₃₀H₃₄ClNO₂
• 分子量: 476.058
• InChiKey: JXZFLDHLLXGLQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  BSc3018 在 sodium thiomethoxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以89%的产率得到BSc4053
  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：

  卡洛芬 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 BSc3018
  参考文献：
  名称：

  Scaffold of the Cyclooxygenase-2 (COX-2) Inhibitor Carprofen Provides Alzheimer γ-Secretase Modulators

  摘要：

  N-Sulfonylated and N-alkylated carprofen derivatives were investigated for their inhibition and modulation of gamma-secretase, which is associated with Alzheimer's disease. The introduction of a lipophilic substituent transformed the COX-2 inhibitor carprofen into a potent gamma-secretase modulator. Several compounds (e.g., 9p, 11f) caused selective reduction of A beta(42) and an increase of A beta(38). The most active compounds displayed activities in the low micromolar range and no effect on the gamma-secretase cleavage at the epsilon-site.

  DOI：

  10.1021/jm0610200

文献信息

• 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.
• Scaffold of the Cyclooxygenase-2 (COX-2) Inhibitor Carprofen Provides Alzheimer γ-Secretase Modulators
  作者：Rajeshwar Narlawar、Blanca I. Pérez Revuelta、Christian Haass、Harald Steiner、Boris Schmidt、Karlheinz Baumann

  DOI：10.1021/jm0610200

  日期：2006.12.1

  N-Sulfonylated and N-alkylated carprofen derivatives were investigated for their inhibition and modulation of gamma-secretase, which is associated with Alzheimer's disease. The introduction of a lipophilic substituent transformed the COX-2 inhibitor carprofen into a potent gamma-secretase modulator. Several compounds (e.g., 9p, 11f) caused selective reduction of A beta(42) and an increase of A beta(38). The most active compounds displayed activities in the low micromolar range and no effect on the gamma-secretase cleavage at the epsilon-site.