ethyl 7-[5-[3-(4-methoxyphenyl)propanoyl]thiophen-3-yl]heptanoate | 146822-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 7-[5-[3-(4-methoxyphenyl)propanoyl]thiophen-3-yl]heptanoate
• CAS: 146822-75-5
• 化学式: C₂₃H₃₀O₄S
• 分子量: 402.555
• InChiKey: YFTVLFNNXMLZLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 7-[5-[3-(4-methoxyphenyl)propanoyl]thiophen-3-yl]heptanoate 在 氢氧化钾 、 一水合肼 作用下， 以 various solvent(s) 为溶剂， 反应 4.0h， 生成 7-<5-<3-(4-hydroxyphenyl)propyl>-3-thienyl>heptanoic acid 、 7-<5-<3-(4-methoxyphenyl)propyl>-3-thienyl>heptanoic 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：

  4-甲氧基苯丙酰氯 、 乙基7-(3-噻吩基)庚酸酯 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 ethyl 7-[5-[3-(4-methoxyphenyl)propanoyl]thiophen-3-yl]heptanoate 、 7-{2-[3-(4-Methoxy-phenyl)-propionyl]-thiophen-3-yl}-heptanoic acid ethyl ester
  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