(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one | 41639-23-0

• 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-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
• 英文别名: (3aR,4R,5R,6aS)-4-(3R-hydroxy-5-phenyl-1E-pentenyl)-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one；(1S,5R,6R,7R)-6-((3S)-3-hydroxy-5-phenyl-1-pentenyl)-7-[(4-phenylbenzoyl)oxy]-2-oxabicyclo[3.3.0]octan-3-one；(3AR,4R,5R,6AS)-4-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate；[(3aR,4R,5R,6aS)-4-[(E,3R)-3-hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate
• CAS: 41639-23-0
• 化学式: C₃₁H₃₀O₅
• 分子量: 482.576
• InChiKey: ONMMRZIJKPIGTG-WYZALSQISA-N

物化性质

• 沸点：
  697.8±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 在 palladium on activated charcoal sodium hydroxide 、 potassium tert-butylate 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 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 、 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 21.5h， 生成 拉坦前列素
  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 磷酸 、 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 为溶剂， 反应 7.0h， 生成 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-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

• Process for the preparation of latanoprost
  申请人：——

  公开号：US20030149294A1

  公开（公告）日：2003-08-07

  Disclosed is a novel process for the preparation of the anti-glaucoma drug Latanoprost, in good yield, in large amounts and with desired purity. Also disclosed are novel intermediates for the above process.

  揭示了一种新颖的制备抗青光眼药物拉唑前列素的方法，产量高，数量大且纯度良好。还披露了上述方法的新颖中间体。
• Bimatoprost crystalline form I
  申请人：Gutman Arie

  公开号：US20090163596A1

  公开（公告）日：2009-06-25

  The invention provides a novel polymorphic form I of crystalline bimatoprost, method for preparation thereof and new crystalline intermediates in the preparation. This form I of crystalline bimatoprost is used in purification of crude bimatoprost and in storage of bimatoprost as active pharmaceutical intermediate. Use of the physical form of bimatoprost in the manufacture of a medicament is also disclosed.

  本发明提供了一种新的多晶型I的晶体双滴眼液的制备方法，以及制备过程中的新晶体中间体。这种多晶型I的晶体双滴眼液可用于粗制双滴眼液的纯化和双滴眼液作为活性制药中间体的储存。本发明还揭示了在制造药物时使用双滴眼液的物理形式。
• Composition and method for the treatment of psoriasis
  申请人：Stjernschantz Johan

  公开号：US20060041016A1

  公开（公告）日：2006-02-23

  The use of a prostaglandin A 2 derivative, and prodrugs of the compound, for the manufacture of a medicament for the treatment and/or alleviation of psoriasis is presented, as well as a method of treatment, involving the topical application of such prostaglandins. Compositions containing a therapeutically active, and physiologically acceptable amount of the above compound or derivatives thereof, as such or in the form of a prodrug, in a suitable vehicle are also described. Importantly, the derivatives can be applied in therapeutically active amounts without or with only minimal side effects, such as hyperemia, irritation or pain.

  本发明提供了一种使用前列腺素A2衍生物及其前药制备药物，用于治疗和/或缓解银屑病的方法，以及涉及该类前列腺素的局部应用的治疗方法。还描述了含有上述化合物或其衍生物的治疗活性和生理上可接受量的组合物，作为前药或本身存在于适当载体中。重要的是，这些衍生物可以在治疗活性剂量下应用，而无需或只有最小的副作用，例如充血、刺激或疼痛。
• Process for the preparation of prostaglandin derivatives
  申请人：Gutman Arie

  公开号：US20050209337A1

  公开（公告）日：2005-09-22

  The invention provides a novel process for the preparation of prostaglandins and analogues thereof, and new crystalline intermediates in the process.

  该发明提供了一种制备前列腺素及其类似物的新工艺，并在该过程中提供了新的晶体中间体。
• Process for the preparation of Latanoprost
  申请人：Gutman Arie

  公开号：US06927300B2

  公开（公告）日：2005-08-09

  Disclosed is a process for the preparation of the anti-glaucoma drug Latanoprost, in good yield, in large amounts and with desired purity. Also disclosed are novel intermediates for the above process.

  本发明公开了一种制备抗青光眼药物拉坦前列素的过程，其产率高、产量大且纯度良好。同时，本发明还公开了上述过程的新型中间体。