methyl 2-[2,5-dimethoxy-4-(2-methoxy-2-oxoethyl)phenyl]acetate | 106591-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-[2,5-dimethoxy-4-(2-methoxy-2-oxoethyl)phenyl]acetate
• 英文别名: dimethyl 2,2'-(2,5-dimethoxy-1,4-phenylene)diacetate；(2,5-dimethoxy-p-phenylene)-di-acetic acid dimethyl ester；(2,5-Dimethoxy-p-phenylen)-di-essigsaeure-dimethylester；Methyl 2-[2,5-dimethoxy-4-(2-methoxy-2-oxoethyl)phenyl]acetate
• CAS: 106591-96-2
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: HAHJHJLBRUZXEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[2,5-dimethoxy-4-(2-methoxy-2-oxoethyl)phenyl]acetate 在 lithium aluminium tetrahydride 、 正丁基锂 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 54.0h， 生成 3-carbazol-9-yl-N-[2-[4-[2-[3-carbazol-9-ylpropyl(methyl)amino]ethyl]-2,5-dimethoxyphenyl]ethyl]-N-methylpropan-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：

  2,5-二甲氧基苯-1,4-二乙腈 在 氢氧化钾 作用下， 生成 methyl 2-[2,5-dimethoxy-4-(2-methoxy-2-oxoethyl)phenyl]acetate
  参考文献：
  名称：

  Priluzkaja; Mel'nikow, Vilniaus Valstybinis Universitetas, Mokslo Darbai, 1957, # 7, p. 229,231, 232

  摘要：

  DOI：

文献信息

• Priluzkaja; Mel'nikow, Vilniaus Valstybinis Universitetas, Mokslo Darbai, 1957, # 7, p. 229,231, 232
  作者：Priluzkaja、Mel'nikow

  DOI：——

  日期：——
• 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.
• Bivalent dopamine agonists with co-operative binding and functional activities at dopamine D2 receptors, modulate aggregation and toxicity of alpha synuclein protein
  作者：Bidyut Dinda、Banibrata Das、Swati Biswas、Horrick Sharma、Christopher Armstrong、Deepthi Yedlapudi、Tamara Antonio、Maarten Reith、Aloke K. Dutta

  DOI：10.1016/j.bmc.2022.117131

  日期：2023.1