1,5-bis(4-(((tert-butyldimethylsilyl)oxy)methyl)phenoxy)pentane | 1417745-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,5-bis(4-(((tert-butyldimethylsilyl)oxy)methyl)phenoxy)pentane
• 英文别名: Tert-butyl-[[4-[5-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]pentoxy]phenyl]methoxy]-dimethylsilane；tert-butyl-[[4-[5-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]pentoxy]phenyl]methoxy]-dimethylsilane
• CAS: 1417745-41-5
• 化学式: C₃₁H₅₂O₄Si₂
• 分子量: 544.922
• InChiKey: LODJXICKZZRIKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-bis(4-(((tert-butyldimethylsilyl)oxy)methyl)phenoxy)pentane 在 potassium hydrogensulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以77%的产率得到((pentane-1,5-diylbis(oxy))bis(4,1-phenylene))dimethanol
  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：

  叔丁基二甲基氯硅烷 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1,5-bis(4-(((tert-butyldimethylsilyl)oxy)methyl)phenoxy)pentane
  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

文献信息

• New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation
  作者：Sergio A. Caldarelli、Siham El Fangour、Sharon Wein、Christophe Tran van Ba、Christian Périgaud、Alain Pellet、Henri J. Vial、Suzanne Peyrottes

  DOI：10.1021/jm3014585

  日期：2013.1.24

  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).