{3-[(1R,2S,3R)-3-Hydroxy-2-((E)-(S)-3-hydroxy-3-methyl-oct-1-enyl)-5-oxo-cyclopentylsulfanyl]-propylsulfanyl}-acetic acid methyl ester | 210818-87-4

• 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: {3-[(1R,2S,3R)-3-Hydroxy-2-((E)-(S)-3-hydroxy-3-methyl-oct-1-enyl)-5-oxo-cyclopentylsulfanyl]-propylsulfanyl}-acetic acid methyl ester
• CAS: 210818-87-4
• 化学式: C₂₀H₃₄O₅S₂
• 分子量: 418.619
• InChiKey: QNIHJARDVSFVGR-LQSZMFBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  27.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {3-[(1R,2S,3R)-3-Hydroxy-2-((E)-(S)-3-hydroxy-3-methyl-oct-1-enyl)-5-oxo-cyclopentylsulfanyl]-propylsulfanyl}-acetic acid methyl ester 在 porcine liver esterase 作用下， 以 phosphate buffer 、 乙醇 为溶剂， 反应 1.0h， 以39%的产率得到{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-3-hydroxy-3-methyl-octyl)-5-oxo-cyclopentylsulfanyl]-propylsulfanyl}-acetic acid
  参考文献：
  名称：

  Design and synthesis of a selective EP4-Receptor agonist. Part 1: discovery of 3,7-DithiaPGE1 derivatives and identification of Their ω chains

  摘要：

  Improvement of EP4-receptor selectivity and the agonist activity by introduction of heteroatoms into the a chain of PGE(1) was investigated. Among the compounds tested, 3,7-dithiaPGE(1) 4a exhibited good EP4-receptor selectivity and agonist activity. Further modification of the omega chain of 3,7-dithiaPGE(1) was performed to improve EP4-receptor selectivity and agonist activity. Of the compounds produced, 16-phenyl-omega-tetranor-3.7-dithiaPGE(1) 4p possessing moderate EP4-receptor selectivity and agonist activity. was identified as a new chemical lead for further optimization by modification of the aromatic moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00351-0
• 作为产物：
  描述：

  {3-[(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-(S)-3-methyl-3-trimethylsilanyloxy-oct-1-enyl)-5-oxo-cyclopentylsulfanyl]-propylsulfanyl}-acetic acid methyl ester 在 (HF)n*pyridine 作用下， 以 吡啶 、 乙腈 为溶剂， 以48%的产率得到{3-[(1R,2S,3R)-3-Hydroxy-2-((E)-(S)-3-hydroxy-3-methyl-oct-1-enyl)-5-oxo-cyclopentylsulfanyl]-propylsulfanyl}-acetic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of a selective EP4-Receptor agonist. Part 1: discovery of 3,7-DithiaPGE1 derivatives and identification of Their ω chains

  摘要：

  Improvement of EP4-receptor selectivity and the agonist activity by introduction of heteroatoms into the a chain of PGE(1) was investigated. Among the compounds tested, 3,7-dithiaPGE(1) 4a exhibited good EP4-receptor selectivity and agonist activity. Further modification of the omega chain of 3,7-dithiaPGE(1) was performed to improve EP4-receptor selectivity and agonist activity. Of the compounds produced, 16-phenyl-omega-tetranor-3.7-dithiaPGE(1) 4p possessing moderate EP4-receptor selectivity and agonist activity. was identified as a new chemical lead for further optimization by modification of the aromatic moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00351-0