ethyl (S)-2-[4,5-bis(octyloxy)-2-hydroxyphenyl]-4,5-dihydro-4-methyl-4-thiazolecarboxylate | 1067643-05-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (S)-2-[4,5-bis(octyloxy)-2-hydroxyphenyl]-4,5-dihydro-4-methyl-4-thiazolecarboxylate
• 英文别名: ethyl (4S)-2-(2-hydroxy-4,5-dioctoxyphenyl)-4-methyl-5H-1,3-thiazole-4-carboxylate
• CAS: 1067643-05-3
• 化学式: C₂₉H₄₇NO₅S
• 分子量: 521.762
• InChiKey: HSQHJOBETNIBPC-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (S)-2-[4,5-bis(octyloxy)-2-hydroxyphenyl]-4,5-dihydro-4-methyl-4-thiazolecarboxylate 在 甲醇 、 sodium hydroxide 、 水 作用下， 反应 16.0h， 以92%的产率得到(S)-2-[4,5-bis(octyloxy)-2-hydroxyphenyl]-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid
  参考文献：
  名称：

  Desferrithiocin Analogues and Nephrotoxicity

  摘要：

  The syntheses of a series of 4'-O-alkylated (S)-4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-4-thiazole-carboxylic acid and 5'-O-alkylated (S)-4,5-dihydro-2-(2,5-dihydroxyphenyl)-4-methyl-4-thiazoleearboxylic acid ligands are described. Their partition between octanol and water, 109 Pap,, is determined, along with their iron-clearing efficiency (ICE) in both non-iron-overloaded, bile duct-cannulated rodents and in iron-overloaded primates. The ligand-promoted biliary ferrokinetics in rats are described for each of the chelators. Plots of log P-app versus ICE in a rodent model for both the 4'-O-alkylated 2,4-dihydroxy and 5'-O-alkylated 2,5-dihydroxy series produced an inverse parabola plot with r(2) values of 0.97 and 0.81, respectively. The plots indicate an optimum log P-app/ICE relationship. Because of the nature of the data spread in the 4'-O-alkylated 2,4-dihydroxy series, it will be used to help assess the origin of nephrotoxicity in desferrithiocin analogues: is toxicity simply related to lipophilicity, ICE, or a combination of these properties?.

  DOI：

  10.1021/jm8003398
• 作为产物：
  描述：

  (S)-2-[4,5-bis(octyloxy)-2-hydroxyphenyl]-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid 、 碘乙烷 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以0.93 g的产率得到ethyl (S)-2-[4,5-bis(octyloxy)-2-hydroxyphenyl]-4,5-dihydro-4-methyl-4-thiazolecarboxylate
  参考文献：
  名称：

  Desferrithiocin Analogues and Nephrotoxicity

  摘要：

  The syntheses of a series of 4'-O-alkylated (S)-4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-4-thiazole-carboxylic acid and 5'-O-alkylated (S)-4,5-dihydro-2-(2,5-dihydroxyphenyl)-4-methyl-4-thiazoleearboxylic acid ligands are described. Their partition between octanol and water, 109 Pap,, is determined, along with their iron-clearing efficiency (ICE) in both non-iron-overloaded, bile duct-cannulated rodents and in iron-overloaded primates. The ligand-promoted biliary ferrokinetics in rats are described for each of the chelators. Plots of log P-app versus ICE in a rodent model for both the 4'-O-alkylated 2,4-dihydroxy and 5'-O-alkylated 2,5-dihydroxy series produced an inverse parabola plot with r(2) values of 0.97 and 0.81, respectively. The plots indicate an optimum log P-app/ICE relationship. Because of the nature of the data spread in the 4'-O-alkylated 2,4-dihydroxy series, it will be used to help assess the origin of nephrotoxicity in desferrithiocin analogues: is toxicity simply related to lipophilicity, ICE, or a combination of these properties?.

  DOI：

  10.1021/jm8003398