(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one | 145773-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
• 英文别名: (3aR,4R,5R,6aS)-4-[3S-hydroxy-5-phenylpentyl]-5-(hydroxy)-hexahydro-2H-cyclopenta[b]furan-2-one；(3AR,4R,5R,6aS)-5-hydroxy-4-((S)-3-hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one；(3aR,4R,5R,6aS)-5-hydroxy-4-[(3S)-3-hydroxy-5-phenylpentyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 145773-21-3
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: CQVHXVLSHMRWEC-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 在 potassium tert-butylate 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 9.5h， 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 palladium on activated charcoal sodium hydroxide 、 磷酸 、 氢气 、 L-Selectride 、 sodium hydride 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 乙醇 为溶剂， 反应 19.0h， 生成 (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-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

• [EN] PREPARATION OF PROSTAGLANDIN DERIVATIVES<br/>[FR] PRÉPARATION DE DÉRIVÉS DE PROSTAGLANDINES
  申请人：APTUIT LAURUS PRIVATE LTD

  公开号：WO2012011128A1

  公开（公告）日：2012-01-26

  A process for preparing the prostaglandin derivatives is provided, wherein the benzoyl and p-nitrobenzoyl groups are used as the hydroxyl protective groups. A pharmaceutical composition comprising the prostaglandin derivatives is also provided.

  提供了一种制备前列腺素衍生物的过程，其中苯甲酰和对硝基苯甲酰基被用作羟基保护基团。同时还提供了一种包含前列腺素衍生物的药物组合物。