(5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester | 208112-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester
• 英文别名: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(3R)-4-(3-chlorophenoxy)-3-fluorobutyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
• CAS: 208112-12-3
• 化学式: C₂₅H₃₆ClFO₅
• 分子量: 471.009
• InChiKey: AMLQVTQWDLJBHH-XNWBWCBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以28%的产率得到(5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid
  参考文献：
  名称：

  15-Fluoro prostaglandin FP agonists: a new class of topical ocular hypotensives

  摘要：

  A novel series of 15-fluoro prostaglandins with phenoxy termination of the omega-chain was synthesized and evaluated for binding and functional activation of the prostaglandin FP receptor in vitro and for side effect potential and topical ocular hypotensive efficacy in vivo. Compounds with the 15alpha-fluoride relative stereochemistry displayed EC50 values of less than or equal to 20 nM, comparable to the value for the endogenous ligand PGF(2alpha). Evaluation of selected ester prodrugs of these 15-fluoro prostaglandins in vivo highlighted their generally low propensity to elicit hyperemia or ocular irritation in rabbits and efficacious intraocular pressure-lowering property in monkeys. In particular 13,14-dihydro-15-deoxy-15alpha-fluoro-16-aryloxy-omega-tetranor-cis-Delta(4) -PGF(2alpha) isopropylester (24) caused relatively little ocular irritation in rabbits while lowering intraocular pressure in conscious ocular hypertensive monkeys by 39% following a topical ocular dose of 3 mug. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.034
• 作为产物：
  描述：

  2H-环戊并[B]呋喃-2-酮,5-(苯甲酰氧基)-4-[(1E)-4-(3-氯苯氧基)-3-氧代-1-丁烯-1-基]六氢,(3AR,4R,5R,6AS)-(...) 在 palladium on activated charcoal 盐酸 、 (+)-β-chlorodiisopinocampheylborane 、 二乙胺基三氟化硫 、 potassium tert-butylate 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 异丙醇 、 丙酮 、 甲苯 为溶剂， 反应 0.25h， 生成 (5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester
  参考文献：
  名称：

  15-Fluoro prostaglandin FP agonists: a new class of topical ocular hypotensives

  摘要：

  A novel series of 15-fluoro prostaglandins with phenoxy termination of the omega-chain was synthesized and evaluated for binding and functional activation of the prostaglandin FP receptor in vitro and for side effect potential and topical ocular hypotensive efficacy in vivo. Compounds with the 15alpha-fluoride relative stereochemistry displayed EC50 values of less than or equal to 20 nM, comparable to the value for the endogenous ligand PGF(2alpha). Evaluation of selected ester prodrugs of these 15-fluoro prostaglandins in vivo highlighted their generally low propensity to elicit hyperemia or ocular irritation in rabbits and efficacious intraocular pressure-lowering property in monkeys. In particular 13,14-dihydro-15-deoxy-15alpha-fluoro-16-aryloxy-omega-tetranor-cis-Delta(4) -PGF(2alpha) isopropylester (24) caused relatively little ocular irritation in rabbits while lowering intraocular pressure in conscious ocular hypertensive monkeys by 39% following a topical ocular dose of 3 mug. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.034