(3aS,4R,5R,6aS)-4-(3-phenoxy-2-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol | 1134877-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3aS,4R,5R,6aS)-4-(3-phenoxy-2-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol
• CAS: 1134877-92-1
• 化学式: C₂₆H₃₈O₈
• 分子量: 478.583
• InChiKey: IEOLUFPMJUVURT-AOISXYONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5R,6aS)-4-(3-phenoxy-2-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol 、 4-羧丁基三苯基溴化膦 在 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.0h， 生成 (Z)-7-[(1S,2R,3R,5S)-5-hydroxy-3-(oxan-2-yloxy)-2-[2-(oxan-2-yloxy)-3-phenoxypropoxy]cyclopentyl]hept-5-enoic acid
  参考文献：
  名称：

  Discovery of 13-oxa prostaglandin analogs as antiglaucoma agents: Synthesis and biological activity

  摘要：

  FP-Class prostaglandin analogs have demonstrated utility for the treatment of glaucoma and ocular hypertension. A series of novel FP prostaglandin analogs was designed to optimize topical ocular activity and reduce ocular side-effects by replacing 13-carbon with oxygen. A facile synthesis was successfully developed for synthesis of the 13-oxa prostaglandins from the commercially available Corey aldehyde benzoate. Among the compounds synthesized, AL-16082 was the most potent prostaglandin FP agonist in vitro. In a prostaglandin FP receptor-linked second-messenger assay, phosphoinositide (PI) turnover, it exhibited a potency value (EC(50)) of 1.9 nM (78% max. response relative to. uprostenol). The isopropyl ester of AL-16082, compound AL-16049, significantly lowered intraocular pressure (IOP) in the ocular hypertensive monkey eyes by 30%. In the study of acute ocular irritation response in New Zealand albino rabbits, AL-16049 produced lower incidence of hyperemia, swelling, and discharge than PGF(2 alpha) (1 mu g), and a similar incidence of hyperemia, swelling, and discharge to latanoprost (1.8 mu g). AL-16049 also produced no signs of ocular irritation or discomfort in the cat at the doses evaluated. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.11.070
• 作为产物：
  描述：

  在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (3aS,4R,5R,6aS)-4-(3-phenoxy-2-((tetrahydro-2H-pyran-2-yl)oxy)propoxy)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol
  参考文献：
  名称：

  Discovery of 13-oxa prostaglandin analogs as antiglaucoma agents: Synthesis and biological activity

  摘要：

  FP-Class prostaglandin analogs have demonstrated utility for the treatment of glaucoma and ocular hypertension. A series of novel FP prostaglandin analogs was designed to optimize topical ocular activity and reduce ocular side-effects by replacing 13-carbon with oxygen. A facile synthesis was successfully developed for synthesis of the 13-oxa prostaglandins from the commercially available Corey aldehyde benzoate. Among the compounds synthesized, AL-16082 was the most potent prostaglandin FP agonist in vitro. In a prostaglandin FP receptor-linked second-messenger assay, phosphoinositide (PI) turnover, it exhibited a potency value (EC(50)) of 1.9 nM (78% max. response relative to. uprostenol). The isopropyl ester of AL-16082, compound AL-16049, significantly lowered intraocular pressure (IOP) in the ocular hypertensive monkey eyes by 30%. In the study of acute ocular irritation response in New Zealand albino rabbits, AL-16049 produced lower incidence of hyperemia, swelling, and discharge than PGF(2 alpha) (1 mu g), and a similar incidence of hyperemia, swelling, and discharge to latanoprost (1.8 mu g). AL-16049 also produced no signs of ocular irritation or discomfort in the cat at the doses evaluated. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.11.070