4-{2-[(1R,2R,3R,5R)-5-Fluoro-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethylsulfanyl}-butyric acid methyl ester | 443147-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{2-[(1R,2R,3R,5R)-5-Fluoro-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethylsulfanyl}-butyric acid methyl ester
• CAS: 443147-12-4
• 化学式: C₃₄H₅₁FO₇S
• 分子量: 622.839
• InChiKey: DOYCIFZKENTEKP-WCGOJINYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  43.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-{2-[(1R,2R,3R,5R)-5-Fluoro-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethylsulfanyl}-butyric acid methyl ester 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 4-(2-{(1R,2R,3R,5R)-5-Fluoro-3-hydroxy-2-[(E)-(S)-3-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-cyclopentyl}-ethylsulfanyl)-butyric acid
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7
• 作为产物：
  描述：

  4-{2-[(1R,2R,3R,5S)-5-Methanesulfonyloxy-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethylsulfanyl}-butyric acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以0.90 g的产率得到4-{2-[(1R,2R,3R,5R)-5-Fluoro-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethylsulfanyl}-butyric acid methyl ester
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7