(16RS)-11-O-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsilyloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester | 433219-70-6

• 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: (16RS)-11-O-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsilyloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester
• CAS: 433219-70-6
• 化学式: C₃₆H₆₆O₅Si₂
• 分子量: 635.088
• InChiKey: LHWQFXRTPFOAFL-DPGBXWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.18
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (16RS)-11-O-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsilyloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 15.0h， 生成 (Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-propyl-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：

  2,2-trimethylene-1-pentanal 在 2,6-二甲基吡啶 、 Schwartz's reagent 、 叔丁基锂 、 magnesium 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 3.01h， 生成 (16RS)-11-O-(tert-butyldimethylsilyl)-15-deoxy-16-(tert-butyldimethylsilyloxy)-17,17-trimethyleneprostaglandin E₂ methyl ester
  参考文献：
  名称：

  Development of a highly selective EP2-receptor agonist. Part 1: identification of 16-hydroxy-17,17-trimethylene PGE2 derivatives

  摘要：

  Design and synthesis of an EP2-receptor selective agonist began with the chemical modification of alpha- and omega-chains of butaprost 1a, which exhibits an affinity for the IP-receptor. Two series of prostaglandin (PG) analogues with a 16-hydroxy-17,17-trimethylene moiety as an omega-chain were identified. Among those tested, 4a,b,e,f,h and 6a,b,e,f,h were found to be highly selective EP2-receptor agonists. Structure activity relationships are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00369-8