17-phenyl-15R-18,19,20-trinor-PGF_2α isopropyl ester | 130273-87-9

• 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: 17-phenyl-15R-18,19,20-trinor-PGF_2α isopropyl ester
• 英文别名: 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester；15(R)-17-Phenyl trinor prostaglandin F2alpha isopropyl ester；propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoate
• CAS: 130273-87-9
• 化学式: C₂₆H₃₈O₅
• 分子量: 430.585
• InChiKey: JGZRPRSJSQLFBO-DYZSFVSISA-N

物化性质

• 溶解度：
  DMF:30.0(最大浓度 mg/mL);69.67(最大浓度 mM)乙醇:30.0(最大浓度 mg/mL);69.67(最大浓度 mM)PBS (pH 7.2) ):1.0(最大浓度 mg/mL);2.32(最大浓度 mM)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17-phenyl-15R-18,19,20-trinor-PGF_2α isopropyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (-)-diisopropyl tartrate 、 双氧水 、 苯硼酸 作用下， 生成 (Z)-7-[(1R,2R,3R,5S)-2-((1R,2S,3R)-1,3-Dihydroxy-5-phenyl-2-phenylsulfanyl-pentyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Reactions of 17-Phenyl-18,19,20-trinorprostaglandin F_2α Isopropyl Ester

  摘要：

  Novel prostaglandin F-2 alpha derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F-2 alpha isopropyl ester [(15S)-1] and its epimer [(15R)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.

  DOI：

  10.1021/jo960098t
• 作为产物：
  描述：

  (Z)-7-[(1R,2R,3S,5S)-3,5-二羟基-2-[(E)-3-羟基-5-苯基戊-1-烯基]环戊基]庚-5-烯酸 在 sodium tetrahydroborate 、 cerium(III) chloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 41.5h， 生成 17-phenyl-15R-18,19,20-trinor-PGF_2α isopropyl ester
  参考文献：
  名称：

  Phenyl-substituted prostaglandins: potent and selective antiglaucoma agents

  摘要：

  A series of phenyl-substituted analogues of prostaglandin F2alpha (PGF2alpha) were prepared and evaluated for ocular hypotensive effect and side effects in different animal models. In addition, the activity of the analogues on FP receptors was studied in vitro. The results were compared with those of PGF2alpha and its isopropyl ester. The phenyl-substituted PGF2alpha analogues exhibited good intraocular pressure reducing effect, were more selective, and exhibited a much higher therapeutic index in the eye than PGF2alpha or its isopropyl ester. The analogues exhibited high activity on FP receptors in a stereoselective manner for the 15alpha-hydroxyl group.

  DOI：

  10.1021/jm00054a008

文献信息

• Process for the synthesis of prostaglandins and intermediates thereof
  申请人：Newchem S.p.A.

  公开号：EP2495235B1

  公开（公告）日：2015-08-05
• Regio- and Stereoselective Reactions of 17-Phenyl-18,19,20-trinorprostaglandin F₂_α Isopropyl Ester
  作者：Charlotta Liljebris、Björn M. Nilsson、Bahram Resul、Uli Hacksell

  DOI：10.1021/jo960098t

  日期：1996.1.1

  Novel prostaglandin F-2 alpha derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F-2 alpha isopropyl ester [(15S)-1] and its epimer [(15R)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.
• Phenyl-substituted prostaglandins: potent and selective antiglaucoma agents
  作者：Bahram Resul、Johan Stjernschantz、Kiyo No、Charlotta Liljebris、Goeran Selen、Maria Astin、Maritha Karlsson、Laszlo Z. Bito

  DOI：10.1021/jm00054a008

  日期：1993.1

  A series of phenyl-substituted analogues of prostaglandin F2alpha (PGF2alpha) were prepared and evaluated for ocular hypotensive effect and side effects in different animal models. In addition, the activity of the analogues on FP receptors was studied in vitro. The results were compared with those of PGF2alpha and its isopropyl ester. The phenyl-substituted PGF2alpha analogues exhibited good intraocular pressure reducing effect, were more selective, and exhibited a much higher therapeutic index in the eye than PGF2alpha or its isopropyl ester. The analogues exhibited high activity on FP receptors in a stereoselective manner for the 15alpha-hydroxyl group.