(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one | 145667-74-9

• 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: (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
• 英文别名: (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7-(4-phenylbenzoyloxy)-2-oxabicyclo<3.3.0>octane-3-one；(1S,5R,6R,7R)-6-[(3R)-3-hydroxy-5-phenyl-1-pentyl]-7-[(4-phenylbenzoyl)oxy]-2-oxabicyclo[3.3.0]octan-3-one；(3AR,4R,5R,6aS)-4-((R)-3-hydroxy-5-phenylpentyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate；[(3aR,4R,5R,6aS)-4-[(3R)-3-hydroxy-5-phenylpentyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate
• CAS: 145667-74-9
• 化学式: C₃₁H₃₂O₅
• 分子量: 484.592
• InChiKey: AAIAETKAOFBTIS-MJOVFQHFSA-N

物化性质

• 溶解度：
  可溶于乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 在 potassium tert-butylate 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 11.5h， 生成 (15S)-拉坦前列素游离酸
  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
• 作为产物：
  描述：

  (3aR,4S,5R,6aS)-(-)-六氢-4-(羟甲基)-2-氧代-2H-环戊并[b]呋喃-5-基 1,1'-联苯-4-甲酸酯 在 palladium on activated charcoal sodium hydroxide 、 磷酸 、 氢气 、 L-Selectride 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 乙醇 为溶剂， 反应 13.0h， 生成 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
  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

• Ligand-controlled palladium-catalyzed intramolecular reactions of phenyl-substituted prostaglandin F2α analogues
  作者：Charlotta Liljebris、Bahram Result、Uli Hacksell

  DOI：10.1016/0040-4020(95)00511-6

  日期：1995.8

  Palladium catalyzed intramolecular cyclizalions of the 15R and 15S epimers of 17-(2-iodophenyl)-18,19,20-trinorprostaglandin F2α isopropylester [(15R)-5 and (15S)-5, respectively] produce a complex mixture of products including various tetrahydronaphthol derivatives and related ketones. The products have been isolated and structurally determined and mechanisms that rationalize their formation are discussed

  钯催化的15分子内cyclizalions ř和15小号的17-（2-碘苯基）-18,19,20-trinorprostaglandin˚F差向异构体2α异丙酯[（15 - [R ）- 5和（15小号） - 5，分别]产生产品的复杂混合物，包括各种四氢萘酚衍生物和相关的酮。产品已被分离出来，并在结构上得到确定，并讨论了合理化其形成机理。该环化反应可被控制，以选择性地通过膦配体的合适的选择主要提供一个或两个环化产物。
• 一种拉坦前列腺素的制备方法
  申请人：西安国康瑞金制药有限公司

  公开号：CN112608294A

  公开（公告）日：2021-04-06

  本发明提供了拉坦前列腺素的制备方法。所述方法使用过渡金属催化剂以引入ω侧链，与现有技术的方法相比，步骤少、产率高、产物纯度高，避免了加氢还原过程以及手性还原或手性拆分过程，成本大幅降低，安全性提高，三废排放量少，环保性高，特别适合于工业化应用以生产拉坦前列腺素。
• [EN] IMPROVED PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND ANALOGUES THEREOF<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE PROSTAGLANDINES ET DE LEURS ANALOGUES
  申请人：MATRIX LAB LTD

  公开号：WO2010109476A3

  公开（公告）日：2012-10-04
• DEUTERIUM-ENRICHED LATANOPROST
  申请人：Czarnik Anthony W.

  公开号：US20090062561A1

  公开（公告）日：2009-03-05

  The present application describes deuterium-enriched latanoprost, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.