(15S)-拉坦前列素游离酸 | 41639-84-3

• 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: (15S)-拉坦前列素游离酸
• 英文名称: (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF_2α
• 英文别名: (15S)-Latanoprost Acid；(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
• CAS: 41639-84-3
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: HNPFPERDNWXAGS-PUJPTKFWSA-N

物化性质

• 沸点：
  609.1±50.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  拉坦前列腺素内半缩醛	(3aR,4R,5R,6aS)-4-[(3R)-3-hydroxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol	352276-28-9	C18H26O4	306.402
  拉坦前列腺素内酯二醇	(3aR,4R,5R,6aS)-5-hydroxy-4-((R)-3-hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one	145667-75-0	C18H24O4	304.386

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  15(S)-拉坦前列素	isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate	145773-22-4	C26H40O5	432.601

反应信息

• 作为反应物：
  描述：

  2-碘代丙烷 、 (15S)-拉坦前列素游离酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以34%的产率得到15(S)-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 、 potassium tert-butylate 、 氢气 、 L-Selectride 、 sodium hydride 、 二异丁基氢化铝 、 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 、 甲苯 为溶剂， 反应 24.5h， 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

文献信息

• Compounds And Compositions for the Treatment of Ocular Disorders
  申请人：Graybug Vision, Inc.

  公开号：US20170080092A1

  公开（公告）日：2017-03-23

  The disclosure describes prodrugs and derivatives of prostaglandins, carbonic anhydrase inhibitors, kinase inhibitors, beta-adrenergic receptor antagonists and other drugs, as well as controlled delivery formulations containing such prodrugs and derivatives, for the treatment of ocular disorders.

  该披露描述了前药和前列腺素的衍生物、碳酸酐酶抑制剂、激酶抑制剂、β-肾上腺素受体拮抗剂和其他药物，以及含有这些前药和衍生物的受控释放配方，用于治疗眼部疾病。
• COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF OCULAR DISORDERS
  申请人：Graybug Vision, Inc.

  公开号：US20180028673A1

  公开（公告）日：2018-02-01

  The disclosure describes prodrugs and derivatives of prostaglandins, carbonic anhydrase inhibitors, kinase inhibitors, beta-adrenergic receptor antagonists and other drugs, as well as controlled delivery formulations containing such prodrugs and derivatives, for the treatment of ocular disorders.
• US9808531B2
  申请人：——

  公开号：US9808531B2

  公开（公告）日：2017-11-07
• US9956302B2
  申请人：——

  公开号：US9956302B2

  公开（公告）日：2018-05-01