N-[2-(4-methoxyphenyl)ethyl]-N'-(1-naphthyl)ethane-1,2-diamine | 1027898-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(4-methoxyphenyl)ethyl]-N'-(1-naphthyl)ethane-1,2-diamine
• 英文别名: N-[2-(4-methoxyphenyl)ethyl]-N'-naphthalen-1-ylethane-1,2-diamine
• CAS: 1027898-33-4
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: VWGMYUHEZAZSET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  33.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙醇 在 正丁基锂 、 五氯化磷 、 calcium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 4.67h， 生成 N-[2-(4-methoxyphenyl)ethyl]-N'-(1-naphthyl)ethane-1,2-diamine
  参考文献：
  名称：

  NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

  摘要：

  Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C-6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli induced increase of C-16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.09.021

文献信息

• PHARMAZEUTISCHE ZUBEREITUNGEN ZUR HEMMUNG VON SPHIMGOMYELINASE
  申请人：Universität Heidelberg

  公开号：EP1207886A2

  公开（公告）日：2002-05-29
• SPHINGOMYELINASE INHIBITOREN ALS WIRKSTOFFE MIT ANTIAPOPTOTISCHER UND ANTISEPTISCHER WIRKUNG
  申请人：Biofrontera Pharmaceuticals GmbH

  公开号：EP1207886B1

  公开（公告）日：2005-11-16
• [DE] SPHINGOMYELINASEHEMMER<br/>[EN] SPHINGOMYELINASE INHIBITOR<br/>[FR] INHIBITEURS DE SPHINGOMYELINASES
  申请人：UNIV HEIDELBERG

  公开号：WO2000072833A2

  公开（公告）日：2000-12-07

  Die vorliegende Erfindung betrifft pharmazeutische Zusammensetzungen mit antiapoptotischer und antiseptischer Wirkung, die als Hemmstoffe der Sphingomyelinasen eingesetzt werden können. Die erfindungsgemässen pharmazeutischen Zusammensetzungen sind insbesondere zur Behandlung von Sepsis, Arteriosklerose, neurodegenerativen Erkrankungen, wie z.B. Morbus Alzheimer, und retroviralen Infektionen, wie z.B. HIV-Infektionen, verwendbar.
• NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation
  作者：Markus Blaess、Nelly Bibak、Ralf A. Claus、Matthias Kohl、Gabriel A. Bonaterra、Ralf Kinscherf、Stefan Laufer、Hans-Peter Deigner

  DOI：10.1016/j.ejmech.2017.09.021

  日期：2018.6

  Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C-6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli induced increase of C-16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus. (C) 2017 Elsevier Masson SAS. All rights reserved.