(Z)-7-{(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(3-ethoxymethyl-phenyl)-3-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester | 261772-73-0

• 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: (Z)-7-{(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(3-ethoxymethyl-phenyl)-3-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester
• CAS: 261772-73-0
• 化学式: C₂₆H₃₇ClO₅
• 分子量: 465.03
• InChiKey: VXIGAFKLKPILLY-CHSMOHKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-{(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(3-ethoxymethyl-phenyl)-3-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到(5Z)-7-((1R,2R,3R,5R)-5-chloro-2-{(1E,3S)-4-[3-(ethoxymethyl)phenyl]-3-hydroxybut-1-enyl}-3-hydroxycyclopentyl)hept-5-enoic 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：

  3-(S)-hydroxy-4-(3-ethoxymethylphenyl)-1-butyne 在 吡啶 、 咪唑 、 Schwartz's reagent 、 四丁基氯化铵 、 叔丁基锂 、 L-Selectride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 为溶剂， 反应 1.0h， 生成 (Z)-7-{(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(3-ethoxymethyl-phenyl)-3-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enoic 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