2,5-bis[4-carboxyphenyl]furan diacid chloride | 101579-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,5-bis[4-carboxyphenyl]furan diacid chloride
• 英文别名: 4-[5-(4-Carbonochloridoylphenyl)furan-2-yl]benzoyl chloride
• CAS: 101579-34-4
• 化学式: C₁₈H₁₀Cl₂O₃
• 分子量: 345.182
• InChiKey: FTGLWJBMVBQDFN-UHFFFAOYSA-N

物化性质

• 沸点：
  475.6±45.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4,4'-(2,5-呋喃二基)二-苯甲腈 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 2,5-bis[4-carboxyphenyl]furan diacid chloride
  参考文献：
  名称：

  SYNTHESIS OF 2,5-BIS-[4-(BENZHYDRAZIDO)-PHENYL]FURANS AND EVALUATION OF THE ANTIMALARIAL, TRYPANOCIDAL, AND CYTOTOXIC ACTIVITIES

  摘要：

  DOI：

  10.1515/hc.2004.10.2-3.157

文献信息

• Del Poeta, Maurizio; Schell, Wiley A.; Dykstra, Christine C., Antimicrobial Agents and Chemotherapy, 1998, vol. 42, # 10, p. 2503 - 2510
  作者：Del Poeta, Maurizio、Schell, Wiley A.、Dykstra, Christine C.、Jones, Susan K.、Tidwell, Richard R.、Kumar, Arvind、Boykin, David W.、Perfect, John R.

  DOI：——

  日期：——
• Inhibition of the HIV-1 rev–RRE complex formation by unfused aromatic cations
  作者：G Xiao

  DOI：10.1016/s0968-0896(00)00344-8

  日期：2001.5

  RNA viruses cause a wide range of human diseases. Development of new agents to target such viruses is an active area of research. Towards this goal, a series of diphenylfuran cations as potential inhibitors of the Rev-RRE complex have been designed and synthesized. Analysis of the interaction of the diphenylfurans with RRE and TAR RNA model systems by gel shift assays indicates that they exhibit both sequence and structure-dependent binding modes. Our results show a strong interaction between the diphenylfuran ring system and RRE bases, while the TAR interactions are much weaker with the compounds that are the best inhibitors of Rev-RRE. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 2,5-Bis[4-(<i>N</i>-alkylamidino)phenyl]furans as Anti-<i>Pneumocystis carinii</i> Agents
  作者：David W. Boykin、Arvind Kumar、Ge Xiao、W. David Wilson、Brendan C. Bender、Donald R. McCurdy、James Edwin Hall、Richard R. Tidwell

  DOI：10.1021/jm970570i

  日期：1998.1.1

  The syntheses of 12 new 2,5-bis[4-(N-alkylamidino)phenyl]furans are reported. The interaction of these dicationic furans with poly(dA-dT) and with the duplex oligomer d(CGCGAATTCGCG)(2) was determined by T-m measurements, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At the screening dose of 10 mu mol/kg, 9 of the 14 N-alkylamidino furans described here are more active than the parent compound 1. Substitution of an alkyl group on the amidino nitrogen, except for in 9, 13, and 15, resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T-m values and suggests enhanced van der Waals interact ions in the bis-amidine-DNA complex. Five of the compounds, 3, 5, 7, 10, and 12, yield cyst counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Five compounds, 1, 6, 8, 10, and 12, show significant activity at a dosage of approximately 1 mu mol/kg; 12 is the most active derivative, and it is approximately 100 times more effective than pentamidine in this animal model.