[1,1'-biphenyl]-4,4'-diylbis(butane-4,1-diyl)bis(4-methylbenzenesulfonate) | 1417745-54-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: [1,1'-biphenyl]-4,4'-diylbis(butane-4,1-diyl)bis(4-methylbenzenesulfonate)
• 英文别名: 4-[4-[4-[4-(4-Methylphenyl)sulfonyloxybutyl]phenyl]phenyl]butyl 4-methylbenzenesulfonate；4-[4-[4-[4-(4-methylphenyl)sulfonyloxybutyl]phenyl]phenyl]butyl 4-methylbenzenesulfonate
• CAS: 1417745-54-0
• 化学式: C₃₄H₃₈O₆S₂
• 分子量: 606.804
• InChiKey: JPDWYXQUMWDYME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1,1'-biphenyl]-4,4'-diylbis(butane-4,1-diyl)bis(4-methylbenzenesulfonate) 、 5-(2-甲氧基乙基)-4-甲基-噻唑 以 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585
• 作为产物：
  描述：

  4,4-二碘联苯 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [1,1'-biphenyl]-4,4'-diylbis(butane-4,1-diyl)bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585