4-[5-(4-carbonazidoylphenyl)furan-2-yl]benzoyl azide | 850360-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 4-[5-(4-carbonazidoylphenyl)furan-2-yl]benzoyl azide
• CAS: 850360-91-7
• 化学式: C₁₈H₁₀N₆O₃
• 分子量: 358.316
• InChiKey: WDYMWGIJHUOECW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  144.8
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[5-(4-carbonazidoylphenyl)furan-2-yl]benzoyl azide 以 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 2,5-bis(4-{3-[2-(1-pyrrolidino)ethyl]ureido}phenyl)furan
  参考文献：
  名称：

  Inhibitory effect of dicationic diphenylfurans on production of type I collagen by human fibroblasts and activated hepatic stellate cells

  摘要：

  Excessive production of extracellular matrix is responsible for clinical manifestations of fibroproliferative disorders and drugs which can inhibit excessive synthesis of type I collagen are needed for the therapy. Several dicationic diphenylfurans were synthesized and were found to bind RNA. Two of these type compounds were able to reduce synthesis of type I collagen by human fibroblasts and human activated hepatic stellate cells (HSCs). Activated HSCs are responsible for collagen production in liver fibrosis. When added at 40 muM compound 588 reduced intracellular level and secretion of procollagen alpha1(I) by 50%, while compound 654 reduced these parameters by more than 80% at 20 muM. 654 also significantly reduced secretion of fibronectin. Toxic effects were observed at 80 muM for 588 and 40 muM for 654. 654 reduced expression of a reporter gene with collagen signal peptide, while expression of the same gene without signal peptide was unaffected. Also, expression of intracellular proteins tubulin and calnexin was unchanged. 654 accumulated inside the cell in the cytoplasm and did not change the steady-state level of collagen mRNAs. Treatment of cells with proteosome inhibitor MG132 did not change the inhibitory effect of 654, suggesting that 654 acts as suppressor of translation of proteins containing a signal peptide. Most secreted proteins of fibroblasts and activated HSCs are components of extracellular matrix. Therefore inhibition of their production, as shown here for procollagen alpha1(I) and fibronectin, may be a useful property of some of diphenylfurans, making these compounds a basis for development of antifibrotic drugs. (C) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2004.09.043
• 作为产物：
  描述：

  2,5-bis[4-carboxyphenyl]furan diacid chloride 在 sodium azide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以93%的产率得到4-[5-(4-carbonazidoylphenyl)furan-2-yl]benzoyl azide
  参考文献：
  名称：

  Inhibitory effect of dicationic diphenylfurans on production of type I collagen by human fibroblasts and activated hepatic stellate cells

  摘要：

  Excessive production of extracellular matrix is responsible for clinical manifestations of fibroproliferative disorders and drugs which can inhibit excessive synthesis of type I collagen are needed for the therapy. Several dicationic diphenylfurans were synthesized and were found to bind RNA. Two of these type compounds were able to reduce synthesis of type I collagen by human fibroblasts and human activated hepatic stellate cells (HSCs). Activated HSCs are responsible for collagen production in liver fibrosis. When added at 40 muM compound 588 reduced intracellular level and secretion of procollagen alpha1(I) by 50%, while compound 654 reduced these parameters by more than 80% at 20 muM. 654 also significantly reduced secretion of fibronectin. Toxic effects were observed at 80 muM for 588 and 40 muM for 654. 654 reduced expression of a reporter gene with collagen signal peptide, while expression of the same gene without signal peptide was unaffected. Also, expression of intracellular proteins tubulin and calnexin was unchanged. 654 accumulated inside the cell in the cytoplasm and did not change the steady-state level of collagen mRNAs. Treatment of cells with proteosome inhibitor MG132 did not change the inhibitory effect of 654, suggesting that 654 acts as suppressor of translation of proteins containing a signal peptide. Most secreted proteins of fibroblasts and activated HSCs are components of extracellular matrix. Therefore inhibition of their production, as shown here for procollagen alpha1(I) and fibronectin, may be a useful property of some of diphenylfurans, making these compounds a basis for development of antifibrotic drugs. (C) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2004.09.043