N,N-dimethyl-3-phenoxazin-10-yl-propan-1-amine | 23690-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: N,N-dimethyl-3-phenoxazin-10-yl-propan-1-amine
• 英文别名: dimethyl-(3-phenoxazin-10-yl-propyl)-amine；10-<(N-Dimetylamino)-propyl>-phenoxazin；10-<3-Dimethylamino-propyl>-phenoxazin；10-(3'-Dimethylamino-propyl)-phenoxazin；10-(3-Dimethylamino-propyl)-phenoxazin；N,N-Dimethyl-3-(10H-phenoxazin-10-yl)propan-1-amine；N,N-dimethyl-3-phenoxazin-10-ylpropan-1-amine
• CAS: 23690-11-1
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: MRRZODWLDXCVIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-3-phenoxazin-10-yl-propan-1-amine 在 正丁基锂 、 三乙胺 作用下， 以 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 53.0h， 生成 N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenoxazin-10-ylpropan-1-amine
  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
• 作为产物：
  描述：

  [1,2,3]triazolo[4,5,1-kl]phenoxazine 在 硫酸 、 铜 作用下， 以 乙醇 为溶剂， 生成 N,N-dimethyl-3-phenoxazin-10-yl-propan-1-amine
  参考文献：
  名称：

  Cieslak,J. et al., Roczniki Chemii, 1960, vol. 34, p. 103 - 110

  摘要：

  DOI：

文献信息

• <i>N</i>-Dimethylaminopropylation in a Solid-Liquid Two Phase System: Synthesis of Chlorpromazine, its Analogs, and Related Compounds
  作者：S. J. Schmolka、Hans Zimmer

  DOI：10.1055/s-1984-30719

  日期：——
• Samolovova,V.G. et al., Journal of general chemistry of the USSR, 1960, vol. 30, p. 1529 - 1531
  作者：Samolovova,V.G. et al.

  DOI：——

  日期：——
• SCHMOLKA, S. J.;ZIMMER, H., SYNTHESIS, BRD, 1984, N 1, 29-31
  作者：SCHMOLKA, S. J.、ZIMMER, H.

  DOI：——

  日期：——
• CN117285481
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.