isopropyl (5Z,9S,11R,15RS)-13-oxa-16-[3-(3-chlorophenoxy)propoxy]-9-hydroxy-11,15-bis(tetrahydro-2H-pyran-2-yl)oxy-17,18,19,20-tetranor-5-prostenoate | 228873-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: isopropyl (5Z,9S,11R,15RS)-13-oxa-16-[3-(3-chlorophenoxy)propoxy]-9-hydroxy-11,15-bis(tetrahydro-2H-pyran-2-yl)oxy-17,18,19,20-tetranor-5-prostenoate
• CAS: 228873-54-9
• 化学式: C₃₄H₅₁ClO₉
• 分子量: 639.227
• InChiKey: PAMBSFRZVMDDCL-HIZISGGKSA-N

反应信息

• 作为反应物：
  描述：

  isopropyl (5Z,9S,11R,15RS)-13-oxa-16-[3-(3-chlorophenoxy)propoxy]-9-hydroxy-11,15-bis(tetrahydro-2H-pyran-2-yl)oxy-17,18,19,20-tetranor-5-prostenoate 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以20 mg的产率得到isopropyl (5Z,9S,11R,15R)-13-oxa-16-[3-(3-chlorophenoxy)propoxy]-9,11,15-trihydroxy-17,18,19,20-tetranor-5-prostenoate
  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：

  2-碘代丙烷 、 (Z)-7-[(1S,2R,3R,5S)-2-[3-(3-chlorophenoxy)-2-(oxan-2-yloxy)propoxy]-5-hydroxy-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoic acid 以0.065 g的产率得到isopropyl (5Z,9S,11R,15RS)-13-oxa-16-[3-(3-chlorophenoxy)propoxy]-9-hydroxy-11,15-bis(tetrahydro-2H-pyran-2-yl)oxy-17,18,19,20-tetranor-5-prostenoate
  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