(Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-isobutyl-cyclobutyl)-but-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester | 433231-80-2

• 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: (Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-isobutyl-cyclobutyl)-but-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester
• CAS: 433231-80-2
• 化学式: C₂₇H₄₄O₆
• 分子量: 464.643
• InChiKey: HCULCZUVMVPUCU-MLJYWJIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-isobutyl-cyclobutyl)-but-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester 在 吡啶 、 2,6-二甲基吡啶 、 氢氟酸 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 22.5h， 生成 (Z)-7-{(1R,2R,3R,5R)-5-Chloro-3-hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-isobutyl-cyclobutyl)-but-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 2: identification of 16-Hydroxy-17,17-trimethylene 9β-chloro PGF derivatives

  摘要：

  Further chemical modification of 1a and 2 was undertaken to identify a more chemically stable selective EP2-receptor agonist for development as a clinical candidate. 9beta-Chloro PG analogues 4a-e and 5a, c-e were found to be potent and selective EP2-receptor agonists. Among them, the compound 4aLy, which is a chemically stabilized lysine salt of 4a, exhibited an excellent profile both in biological activities and physicochemical properties. The agonist 4aLy was found to suppress uterine motility in anesthetized pregnant rats, while PGE(2) stimulated uterine motility. Structure-activity relationships (SARs) are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00370-4
• 作为产物：
  描述：

  (Z)-7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-isobutyl-cyclobutyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 13.5h， 生成 (Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-isobutyl-cyclobutyl)-but-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 2: identification of 16-Hydroxy-17,17-trimethylene 9β-chloro PGF derivatives

  摘要：

  Further chemical modification of 1a and 2 was undertaken to identify a more chemically stable selective EP2-receptor agonist for development as a clinical candidate. 9beta-Chloro PG analogues 4a-e and 5a, c-e were found to be potent and selective EP2-receptor agonists. Among them, the compound 4aLy, which is a chemically stabilized lysine salt of 4a, exhibited an excellent profile both in biological activities and physicochemical properties. The agonist 4aLy was found to suppress uterine motility in anesthetized pregnant rats, while PGE(2) stimulated uterine motility. Structure-activity relationships (SARs) are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00370-4