(5Z,13E,15S)-15-羟基-9-氧代前列腺-5,13-二烯-1-酸 | 35536-53-9

• 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: (5Z,13E,15S)-15-羟基-9-氧代前列腺-5,13-二烯-1-酸
• 英文名称: 11-Deoxy-PGE2
• 英文别名: 11-deoxyprostaglandin E₂；WY-18189；(Z)-7-[(1R,2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
• CAS: 35536-53-9
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: CTHZICXYLKQMKI-FOSBLDSVSA-N

物化性质

• 沸点：
  510.3±45.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：>100 mg/ml（来自 PGE2）； DMSO：>100 mg/ml（来自 PGE2）；乙醇：>100 mg/ml（来自 PGE2）； PBS pH 7.2：>5 mg/ml（来自 PGE2）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5Z,13E,15S)-15-羟基-9-氧代前列腺-5,13-二烯-1-酸 在 吡啶 作用下， 生成 N-{(Z)-7-[(1R,2R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-hept-5-enoyl}-methanesulfonamide
  参考文献：
  名称：

  DE2629834

  摘要：

  公开号：

文献信息

• Treatment of gastric inflammatory disease with cytoprotective prostaglandins and histamine-2 blocking anti-secretory agents
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0108452A1

  公开（公告）日：1984-05-16

  Compositions comprising gastric cytoprotective prostaglandin or prostaglandin-like compounds and histamine-2 receptor blocking anti-secretory agents useful in the treatment and prophylaxis of gastric inflammatory conditions are disclosed. These compositions are effective in the treatment and prophylaxis of gastro-intestinal ulceration. They utilize levels of both prostaglandin and anti-secretory agents which are significantly lower than ordinarily required as the prostaglandin potentiates the effect of the anti-secretory agent, and minimizes the side effects which are frequently associated with the administration of prostaglandins. The method of treating and preventing gastric inflammatory diseases using these compositions is also disclosed.

  本发明公开了由胃细胞保护性前列腺素或前列腺素样化合物和组胺-2 受体阻断抗分泌剂组成的组合物，可用于治疗和预防胃部炎症。这些组合物对治疗和预防胃肠道溃疡有效。它们所使用的前列腺素和抗分泌剂的水平大大低于通常所需的水平，因为前列腺素能增强抗分泌剂的作用，并能最大限度地减少与使用前列腺素有关的副作用。此外，还公开了使用这些组合物治疗和预防胃炎疾病的方法。
• PROSTAGLANDIN RECEPTOR AGONISTS FOR USE IN THE TREATMENT OF A CORONAVIRUS INFECTION SUCH AS COVID-19
  申请人：Medetia

  公开号：EP3981410A1

  公开（公告）日：2022-04-13

  The present invention relates to prostaglandin receptor agonists, such as EP2 and/or EP4 agonists, preferably EP2 agonists, for treating a disease caused by a coronavirus infection, such as COVID-19, in a subject in need thereof, especially in a subject at risk to develop a severe form and/or a complication of said disease.

  本发明涉及前列腺素受体激动剂，如EP2和/或EP4激动剂，优选EP2激动剂，用于治疗由冠状病毒感染（如COVID-19）引起的疾病，适用于有需要的受试者，特别是有可能患上上述疾病的严重形式和/或并发症的受试者。
• Anti-inflammatory Constituents of the Red Alga <i>Gracilaria verrucosa</i> and Their Synthetic Analogues
  作者：Hung The Dang、Hye Ja Lee、Eun Sook Yoo、Pramod B. Shinde、Yoon Mi Lee、Jongki Hong、Dong Kyoo Kim、Jee H. Jung

  DOI：10.1021/np070452q

  日期：2008.2.1

  A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11 -deoxyprostaglandins (1-4), a ceramide (5), and a C-16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.
• COMBINATIONS OF PROSTAGLANDINS AND CLONIDINE DERIVATIVES FOR THE TREATMENT OF GLAUCOMA
  申请人：ALCON LABORATORIES, INC.

  公开号：EP0664707A1

  公开（公告）日：1995-08-02
• KEY INTERMEDIATE FOR SYNTHESIS OF PROSTAGLANDIN COMPOUND AND PREPARATION METHOD THEREOF
  申请人：SHENZHEN CATALYS TECHNOLOGY CO., LTD

  公开号：US20220281797A1

  公开（公告）日：2022-09-08

  The present invention relates to the technical field of organic chemical engineering, and in particular to a key intermediate for synthesizing prostaglandin compounds and a preparation method therefor. When applied to the synthesis of prostaglandin compounds, the process flow is simplified, the yield and product purity are improved, the production costs are reduced, and the industrial application is easy.