(5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester | 733037-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester
• CAS: 733037-34-8
• 化学式: C₃₁H₄₂F₄O₆
• 分子量: 586.664
• InChiKey: RLSZRSBLFXDQHG-LNFHOSTBSA-N

反应信息

• 作为反应物：
  描述：

  (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester 在 盐酸 、 lithium hydroxide 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 生成 (5Z,13E)-(9S,11R,15R)-9,11-dihydroxy-15-fluoro-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranor-5,13-prostadienoic 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：

  [3aR,4R(1E,3RS),5R,6aS]-4-[3-fluoro-4-(3-(trifluoromethyl)phenoxy)-1-buten-1-yl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one 在 potassium tert-butylate 、 二异丁基氢化铝 、 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 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 0.25h， 生成 (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranor-5,13-prostadienoic 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