1,3-双(4-甲氧羰基苯基)丙烷 | 75908-68-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3-双(4-甲氧羰基苯基)丙烷
• 英文名称: 1,3-bis(4-methoxycarbonylphenyl)propane
• 英文别名: 4,4'-propanediyl-di-benzoic acid dimethyl ester；4,4'-Propandiyl-di-benzoesaeure-dimethylester；4,4'-(1,3-propanediyl)bis-benzoic acid, dimethyl ester；Dimethyl 4,4'-(propane-1,3-diyl)dibenzoate；methyl 4-[3-(4-methoxycarbonylphenyl)propyl]benzoate
• CAS: 75908-68-8
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: VEZONEJXOPSUHU-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(Solv: methanol (67-56-1))
• 沸点：
  438.8±38.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-双(4-甲氧羰基苯基)丙烷 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,3-双(4-氯甲基苯基)丙烷
  参考文献：
  名称：

  Synthesis and Structure–Activity Analysis of New Phosphonium Salts with Potent Activity against African Trypanosomes

  摘要：

  A series of 73 bisphosphonium salts and 10 mono-phosphonium salt derivatives were synthesized and tested in vitro against several wild type and resistant lines of Trypanosoma brucei (T. b. rhodesiense STIB900, T. b. brucei strain 427, TbAT1-KO, and TbB48). More than half of the compounds tested showed a submicromolar EC50 against these parasites. The compounds did not display any cross-resistance to existing diamidine therapies, such as pentamidine. In most cases, the compounds displayed a good selectivity index versus human cell lines. None of the known T. b. brucei drug transporters were required for trypanocidal activity, although some of the bisphosphonium compounds inhibited the low affinity pentamidine transporter. It was found that phosphonium drugs act slowly to clear a trypanosome population but that only a short exposure time is needed for irreversible damage to the cells. A comparative molecular field analysis model (CoMFA) was generated to gain insights into the SAR of this class of compounds, identifying key features for trypanocidal activity.

  DOI：

  10.1021/jm2014259
• 作为产物：
  描述：

  1,3-二苯丙烷 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 1,3-双(4-甲氧羰基苯基)丙烷
  参考文献：
  名称：

  Synthesis and Structure–Activity Analysis of New Phosphonium Salts with Potent Activity against African Trypanosomes

  摘要：

  A series of 73 bisphosphonium salts and 10 mono-phosphonium salt derivatives were synthesized and tested in vitro against several wild type and resistant lines of Trypanosoma brucei (T. b. rhodesiense STIB900, T. b. brucei strain 427, TbAT1-KO, and TbB48). More than half of the compounds tested showed a submicromolar EC50 against these parasites. The compounds did not display any cross-resistance to existing diamidine therapies, such as pentamidine. In most cases, the compounds displayed a good selectivity index versus human cell lines. None of the known T. b. brucei drug transporters were required for trypanocidal activity, although some of the bisphosphonium compounds inhibited the low affinity pentamidine transporter. It was found that phosphonium drugs act slowly to clear a trypanosome population but that only a short exposure time is needed for irreversible damage to the cells. A comparative molecular field analysis model (CoMFA) was generated to gain insights into the SAR of this class of compounds, identifying key features for trypanocidal activity.

  DOI：

  10.1021/jm2014259

文献信息

• Stable Organic Biradicals
  作者：GILBERT J. SLOAN、WYMAN R. VAUGHAN

  DOI：10.1021/jo01358a009

  日期：1957.7
• Macro Rings. I. Preparation and Spectra of the Paracyclophanes
  作者：Donald J. Cram、H. Steinberg

  DOI：10.1021/ja01156a059

  日期：1951.12
• Synthesis and Structure–Activity Analysis of New Phosphonium Salts with Potent Activity against African Trypanosomes
  作者：Andrea Taladriz、Alan Healy、Eddysson J. Flores Pérez、Vanessa Herrero García、Carlos Ríos Martínez、Abdulsalam A. M. Alkhaldi、Anthonius A. Eze、Marcel Kaiser、Harry P. de Koning、Antonio Chana、Christophe Dardonville

  DOI：10.1021/jm2014259

  日期：2012.3.22

  A series of 73 bisphosphonium salts and 10 mono-phosphonium salt derivatives were synthesized and tested in vitro against several wild type and resistant lines of Trypanosoma brucei (T. b. rhodesiense STIB900, T. b. brucei strain 427, TbAT1-KO, and TbB48). More than half of the compounds tested showed a submicromolar EC50 against these parasites. The compounds did not display any cross-resistance to existing diamidine therapies, such as pentamidine. In most cases, the compounds displayed a good selectivity index versus human cell lines. None of the known T. b. brucei drug transporters were required for trypanocidal activity, although some of the bisphosphonium compounds inhibited the low affinity pentamidine transporter. It was found that phosphonium drugs act slowly to clear a trypanosome population but that only a short exposure time is needed for irreversible damage to the cells. A comparative molecular field analysis model (CoMFA) was generated to gain insights into the SAR of this class of compounds, identifying key features for trypanocidal activity.