2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: (2E)-2-[(3,5-dimethoxyphenyl)methylidene]-6,7-dimethoxy-3,4-dihydronaphthalen-1-one
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: GHAJFLOZIHUGDL-VIZOYTHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2-[1-(3,5-Dihydroxy-phenyl)-meth-(E)-ylidene]-6,7-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Modulation of Ceramide-Activated Protein Phosphatase 2A Activity by Low Molecular Weight Aromatic Compounds

  摘要：

  Protein phosphatase 2A (PP2A) is one of the most important and abundant serine/threonine phosphatases in mammalian tissues and plays a role in gene expression, cell division, and signal transduction. PP2A is activated by ceramide, which is produced by the hydrolysis of membrane sphingomyelin in response to a variety of stress-related stimuli. To further study the role of ceramide-mediated signal transduction in cellular processes such as senescence and apoptosis, we designed and synthesized a series of low molecular weight aromatic compounds, mainly of the isoquinolone and tetralone classes, and evaluated their ability to inhibit enzymes known to be activated by ceramide. Those enzymes studied were ceramide-activated protein kinase, protein kinase C zeta and PP2A. Of these, only PP2A was found re, be inhibited. A few of the compounds inhibited both ceramide-activated as well as basal PP2A activity. In addition, several of the compounds activated PP2A by up to 300% above basal enzyme activity, but only in the presence of ceramide. Thus, modulation (both inhibition and activation) of the catatylic activity of ceramide-activated PP2A is demonstrated by certain low molecular weight aromatic compounds. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(97)00685-0
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 6,7-二甲氧基-3,4-二氢-2H-1-萘酮 生成 2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Rational design, synthesis and structure–activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones

  摘要：

  Novel substituted 6,7-dimethoxy-1-tetralones and 5,6-dimethoxy-1-indanones have been synthesized and evaluated for their cytotoxicity. Compounds with 3'-lipophilic. 3',5'-dilipophilic, or 3',5'-dilipophilic-4'-hydrophilic substituents on (E)-2-benzylidene moiety showed highly cytotoxic effects. The unique structure of 42 possibly matches the pharmacophore features for these cytotoxic compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00032-9

文献信息

• INADONE AND TETRALONE COMPOUNDS FOR INHIBITING CELL PROLIFERATION
  申请人：The Regents of the University of California

  公开号：EP1039897B1

  公开（公告）日：2006-04-12
• US6162810A
  申请人：——

  公开号：US6162810A

  公开（公告）日：2000-12-19
• Rational design, synthesis and structure–activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones
  作者：Hsiencheng Shih、Lynn Deng、Carlos J Carrera、Souichi Adachi、Howard B Cottam、Dennis A Carson

  DOI：10.1016/s0960-894x(00)00032-9

  日期：2000.3

  Novel substituted 6,7-dimethoxy-1-tetralones and 5,6-dimethoxy-1-indanones have been synthesized and evaluated for their cytotoxicity. Compounds with 3'-lipophilic. 3',5'-dilipophilic, or 3',5'-dilipophilic-4'-hydrophilic substituents on (E)-2-benzylidene moiety showed highly cytotoxic effects. The unique structure of 42 possibly matches the pharmacophore features for these cytotoxic compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Modulation of Ceramide-Activated Protein Phosphatase 2A Activity by Low Molecular Weight Aromatic Compounds
  作者：Lorenzo M. Leoni、Hsien C. Shih、Lynn Deng、Chuck Tuey、Gernot Walter、Dennis A. Carson、Howard B. Cottam

  DOI：10.1016/s0006-2952(97)00685-0

  日期：1998.4

  Protein phosphatase 2A (PP2A) is one of the most important and abundant serine/threonine phosphatases in mammalian tissues and plays a role in gene expression, cell division, and signal transduction. PP2A is activated by ceramide, which is produced by the hydrolysis of membrane sphingomyelin in response to a variety of stress-related stimuli. To further study the role of ceramide-mediated signal transduction in cellular processes such as senescence and apoptosis, we designed and synthesized a series of low molecular weight aromatic compounds, mainly of the isoquinolone and tetralone classes, and evaluated their ability to inhibit enzymes known to be activated by ceramide. Those enzymes studied were ceramide-activated protein kinase, protein kinase C zeta and PP2A. Of these, only PP2A was found re, be inhibited. A few of the compounds inhibited both ceramide-activated as well as basal PP2A activity. In addition, several of the compounds activated PP2A by up to 300% above basal enzyme activity, but only in the presence of ceramide. Thus, modulation (both inhibition and activation) of the catatylic activity of ceramide-activated PP2A is demonstrated by certain low molecular weight aromatic compounds. (C) 1998 Elsevier Science Inc.