(Z)-7-[(1R,2R,3R,5S)-3,5-二羟基-2-[(E)-3-氧代-5-苯基戊-1-烯基]环戊基]庚-5-烯酸丙-2-基酯 | 130209-77-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (Z)-7-[(1R,2R,3R,5S)-3,5-二羟基-2-[(E)-3-氧代-5-苯基戊-1-烯基]环戊基]庚-5-烯酸丙-2-基酯
• 英文名称: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester
• 英文别名: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoate
• CAS: 130209-77-7
• 化学式: C₂₆H₃₆O₅
• 分子量: 428.569
• InChiKey: GKTGBSHVNAVDCL-VCAADEISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-7-[(1R,2R,3R,5S)-3,5-二羟基-2-[(E)-3-氧代-5-苯基戊-1-烯基]环戊基]庚-5-烯酸丙-2-基酯 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 (-)-diisopropyl tartrate 、 双氧水 、 苯硼酸 作用下， 反应 8.5h， 生成 (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((1S,2R,3R)-1,2,3-trihydroxy-5-phenyl-pentyl)-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 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 、 丙酮 为溶剂， 反应 34.0h， 生成 (Z)-7-[(1R,2R,3R,5S)-3,5-二羟基-2-[(E)-3-氧代-5-苯基戊-1-烯基]环戊基]庚-5-烯酸丙-2-基酯
  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