3,7-dithia-16-cyclohexyl-ω-tetranorprostaglandin E₁ methyl ester | 210819-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-dithia-16-cyclohexyl-ω-tetranorprostaglandin E₁ methyl ester
• 英文别名: methyl 2-[3-[(1R,2S,3R)-2-[(E,3S)-4-cyclohexyl-3-hydroxybut-1-enyl]-3-hydroxy-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate
• CAS: 210819-00-4
• 化学式: C₂₁H₃₄O₅S₂
• 分子量: 430.63
• InChiKey: NRFJUXOTDYYYPL-JBJYQZIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,7-dithia-16-cyclohexyl-ω-tetranorprostaglandin E₁ methyl ester 在 porcine liver esterase 作用下， 以 phosphate buffer 、 乙醇 为溶剂， 以34%的产率得到{3-[(1R,2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-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：

  3,7-dithia-16-cyclohexyl-ω-tetranorPGE₁ methyl ester 11,15-bis(tert-butyldimethylsilyl ether) 在 (HF)n*pyridine 作用下， 以 吡啶 、 乙腈 为溶剂， 以63%的产率得到3,7-dithia-16-cyclohexyl-ω-tetranorprostaglandin E₁ 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