ethyl 6-[5-methyl-3-(3-phenylpropyl)thiophen-2-yl]sulfanylhexanoate | 142423-07-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 6-[5-methyl-3-(3-phenylpropyl)thiophen-2-yl]sulfanylhexanoate
• CAS: 142423-07-2
• 化学式: C₂₂H₃₀O₂S₂
• 分子量: 390.611
• InChiKey: CGDMUXGBUVNXCB-UHFFFAOYSA-N

物化性质

• 沸点：
  481.2±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  26.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-[5-methyl-3-(3-phenylpropyl)thiophen-2-yl]sulfanylhexanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 6-<<5-methyl-3-(3-phenylpropyl)-2-thienyl>thio>hexanoic acid
  参考文献：
  名称：

  .omega.-[(.omega.-Arylalkyl)thienyl]alkanoic acids: from specific LTA4 hydrolase inhibitors to LTB4 receptor antagonists

  摘要：

  A series of omega-[(omega-arylalkyl)thienyl]alkanoic acid isomers was prepared and a structure-activity relationship was investigated. These compounds have displayed either LTA, hydrolase inhibition activities or LTB4 receptor binding activities, or both, depending on the relative orientation of the two side chains on the thiophene ring. Whereas the 2,5-isomers specifically exhibited LTA4 hydrolase inhibition, 3,5-isomers displayed both activities. On the other hand, the ''ortho-isomers'' specifically inhibited the binding of the LTB4 to its receptor. The side-chain lengths were also important for an optimal inhibition or binding activity. Substitutions on the terminal aromatic ring or on the thiophene nucleus led to small changes in both activities. The most dramatic effect was obtained by substituting the carboxylic acid side chain in the alpha-position with one or two methyl groups, which substantially enhanced the LTB4 receptor binding activity. In the most favorable case, the alpha,alpha-dimethyl derivative RP66153 was found 20-fold more potent than its linear counterpart.

  DOI：

  10.1021/jm00095a011
• 作为产物：
  描述：

  2-methyl-4-(3-phenylpropyl)thiophene 在 正丁基锂 、 sulfur 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 16.75h， 生成 ethyl 6-[5-methyl-3-(3-phenylpropyl)thiophen-2-yl]sulfanylhexanoate
  参考文献：
  名称：

  .omega.-[(.omega.-Arylalkyl)thienyl]alkanoic acids: from specific LTA4 hydrolase inhibitors to LTB4 receptor antagonists

  摘要：

  A series of omega-[(omega-arylalkyl)thienyl]alkanoic acid isomers was prepared and a structure-activity relationship was investigated. These compounds have displayed either LTA, hydrolase inhibition activities or LTB4 receptor binding activities, or both, depending on the relative orientation of the two side chains on the thiophene ring. Whereas the 2,5-isomers specifically exhibited LTA4 hydrolase inhibition, 3,5-isomers displayed both activities. On the other hand, the ''ortho-isomers'' specifically inhibited the binding of the LTB4 to its receptor. The side-chain lengths were also important for an optimal inhibition or binding activity. Substitutions on the terminal aromatic ring or on the thiophene nucleus led to small changes in both activities. The most dramatic effect was obtained by substituting the carboxylic acid side chain in the alpha-position with one or two methyl groups, which substantially enhanced the LTB4 receptor binding activity. In the most favorable case, the alpha,alpha-dimethyl derivative RP66153 was found 20-fold more potent than its linear counterpart.

  DOI：

  10.1021/jm00095a011