(5Z,8Xi,13E)-9,15-二羟基-N-(2-羟基乙基)-11-氧代前列腺-5,13-二烯-1-酰胺 | 398138-28-8

• 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,8Xi,13E)-9,15-二羟基-N-(2-羟基乙基)-11-氧代前列腺-5,13-二烯-1-酰胺
• 英文名称: Prostaglandin D2 Ethanolamide
• 英文别名: (Z)-N-(2-hydroxyethyl)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enamide
• CAS: 398138-28-8
• 化学式: C₂₂H₃₇NO₅
• 分子量: 395.5
• InChiKey: KEYDJKSQFDUAGF-YIRKRNQHSA-N

物化性质

• 沸点：
  630.7±55.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：8.3 mg/ml； DMSO：8.3 mg/ml；乙醇：12.5 mg/ml； PBS (7.2)：2.5 mg/ml
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氢(+1)阳离子 、 NADPH(4-) 、 (5Z,8Xi,13E)-9,15-二羟基-N-(2-羟基乙基)-11-氧代前列腺-5,13-二烯-1-酰胺 生成 11beta-PGF2alpha-EA 、 NADP⁺
  参考文献：
  名称：

  Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS

  摘要：

  Prostaglandin (PG) D-2 ethanolamide (prostamide D-2) was reduced to 9alpha, 11beta-PGF(2) ethanolamide (9alpha, 11beta-prostamide F-2) by PGF synthase, which also catalyzes the reduction of PGH(2) and PGD(2) to PGF(2alpha) and 9alpha11beta-PGF(2), respectively. These enzyme activities were measured by a new method, the liquid chromatographic-electrospray ionization-mass spectrometry (LC/ESI/MS) technique, which could simultaneously detect the substrate and all products. PGF(2alpha), 9alpha,l lbeta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2 were separated on a TSKgel ODS 80Ts column, ionized by electrospray, and detected in the negative mode. Selected ion monitoring (SIM) of m/z 353 ([M-H](-)), 353 ([M-H](-)), 351 ([M-H](-)) 333 ([M-H-H2O](-)) 456 ([M+59](-)), and m/z 358 ([M-37](-)) was used for quantifying PGF(2alpha), 9alpha,11beta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2, respectively. The detection limit for PGF(2alpha) and 9alpha,11beta-PGF(2) was 0.01 pmol, that for PGH(2) and PGD(2), 0.1 pmol; and that for prostamide D-2 and 9alpha,11beta-prostamide F-2, 0.5 and 0.03 pmol, respectively. The LC/ESI/MS technique for measuring PGF synthase activity showed higher sensitivity than other methods. Using this method, we found that Bimatoprost, the ethyl amide analog of 17-phenyl-trinor PGF(2alpha) and an anti-glaucoma agent, inhibited all three reductase activities of PGF synthase when used at a low concentration. These results suggest that Bimatoprost also behaves as a potent PGF synthase inhibitor in addition to having prostamide-like activity. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2004.02.009

文献信息

• PROSTAGLANDIN ANALOGS AND USES THEREOF
  申请人：Lifex Biolabs, Inc.

  公开号：US20210139435A1

  公开（公告）日：2021-05-13

  The present invention relates to pharmaceutical composition for the prevention or treatment of a disease, disorder, or condition associated with Nurr1, including, as an active ingredient, a prostaglandin analog or a pharmaceutically acceptable salt thereof, wherein the compound has excellent effects in inducing Nurr1, and thus, can be useful as a pharmaceutical composition for the prevention or treatment of a disease, disorder, or condition associated with Nurr1, in particular, cancer, autoimmune disease such as rheumatoid arthritis, schizophrenia, manic depression and neurodegenerative disease such as Alzheimers disease or Parkinson's disease.

  本发明涉及一种药物组合物，用于预防或治疗与Nurr1相关的疾病、紊乱或状况，其中包括作为活性成分的前列腺素类似物或其药学上可接受的盐，该化合物具有良好的诱导Nurr1的效果，因此，可用作预防或治疗与Nurr1相关的疾病、紊乱或状况的药物组合物，特别是癌症、自身免疫性疾病如类风湿关节炎、精神分裂症、躁郁症以及神经退行性疾病如阿尔茨海默病或帕金森病。
• J-series prostaglandin-ethanolamides as novel therapeutics for skin and/or oral disorders
  申请人：East Carolina University

  公开号：US10960013B2

  公开（公告）日：2021-03-30

  Provided is a method of preventing and/or treating a skin disorder and/or an oral disorder including administering to a subject in need thereof an effective amount of a compound of formula (I) or a prodrug or derivative thereof, and salts thereof.

  本发明提供了一种预防和/或治疗皮肤疾病和/或口腔疾病的方法，包括向有需要的受试者施用有效量的式（I）化合物或其原药或衍生物及其盐类。
• J-SERIES PROSTAGLANDIN-ETHANOLAMIDES AS NOVEL THERAPEUTICS FOR SKIN AND/OR ORAL DISORDERS
  申请人：East Carolina University

  公开号：US20210177864A1

  公开（公告）日：2021-06-17

  Provided is a method of preventing and/or treating a skin disorder and/or an oral disorder including administering to a subject in need thereof an effective amount of a compound of formula (I): or a prodrug or derivative thereof, and salts thereof.
• Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS
  作者：Noriko Koda、Yasutaka Tsutsui、Haruki Niwa、Seiji Ito、David F Woodward、Kikuko Watanabe

  DOI：10.1016/j.abb.2004.02.009

  日期：2004.4

  Prostaglandin (PG) D-2 ethanolamide (prostamide D-2) was reduced to 9alpha, 11beta-PGF(2) ethanolamide (9alpha, 11beta-prostamide F-2) by PGF synthase, which also catalyzes the reduction of PGH(2) and PGD(2) to PGF(2alpha) and 9alpha11beta-PGF(2), respectively. These enzyme activities were measured by a new method, the liquid chromatographic-electrospray ionization-mass spectrometry (LC/ESI/MS) technique, which could simultaneously detect the substrate and all products. PGF(2alpha), 9alpha,l lbeta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2 were separated on a TSKgel ODS 80Ts column, ionized by electrospray, and detected in the negative mode. Selected ion monitoring (SIM) of m/z 353 ([M-H](-)), 353 ([M-H](-)), 351 ([M-H](-)) 333 ([M-H-H2O](-)) 456 ([M+59](-)), and m/z 358 ([M-37](-)) was used for quantifying PGF(2alpha), 9alpha,11beta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2, respectively. The detection limit for PGF(2alpha) and 9alpha,11beta-PGF(2) was 0.01 pmol, that for PGH(2) and PGD(2), 0.1 pmol; and that for prostamide D-2 and 9alpha,11beta-prostamide F-2, 0.5 and 0.03 pmol, respectively. The LC/ESI/MS technique for measuring PGF synthase activity showed higher sensitivity than other methods. Using this method, we found that Bimatoprost, the ethyl amide analog of 17-phenyl-trinor PGF(2alpha) and an anti-glaucoma agent, inhibited all three reductase activities of PGF synthase when used at a low concentration. These results suggest that Bimatoprost also behaves as a potent PGF synthase inhibitor in addition to having prostamide-like activity. (C) 2004 Elsevier Inc. All rights reserved.