10β-hydroxy-17β-butoxy-1,4-estradiene-3-one | 612500-19-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 10β-hydroxy-17β-butoxy-1,4-estradiene-3-one
• 英文别名: 10β-hydroxy-17β-butoxyestra-1,4-diene-3-one；(8S,9S,10S,13S,14S,17S)-17-butoxy-10-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 612500-19-3
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: GLAWPRNOLUYCBS-KKFDQILXSA-N

物化性质

• 沸点：
  493.1±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  17β-butoxy-1,3,5(10)-estratrien-3-ol 在 双氧水 、 iron(II) sulfate 作用下， 以 硫酸 为溶剂， 反应 1.0h， 生成 10β-hydroxy-17β-butoxy-1,4-estradiene-3-one
  参考文献：
  名称：

  Mechanistic investigations on the antioxidant action of a neuroprotective estrogen derivative

  摘要：

  Antioxidant action is an important component of the complex neuroprotective effect of estrogens. Combining theoretical prediction and subsequent experimental confirmation by chemical and in vitro paradigms, this study focused on the mechanistic aspects of hydroxyl radical scavenging by 17 beta-butoxy-1,3,5(10)-estratrien-3-ol, a synthetic derivative of 17 beta-estradiol with increased potency to inhibit lipid peroxidation and reduced affinity to estrogen-receptors compared to the endogenous hormone. In the process that acts as a "chemical shield," the phenolic A-ring turns into 10 beta-hydroxy-17 beta-butoxy-1,3,5(10)-estratrien-3-one, a non-aromatic paro-quinol, upon capturing hydroxyl radicals, which results in the complete loss of estrogen-receptor affinity and antioxidant activity. However, the parent compound is apparently recovered in brain tissue from this para-quinol via enzyme-catalyzed NAD(P)H-dependent reductive aromatization without causing oxidative stress. Taken together, our report argues for a previously unrecognized antioxidant cycle for estrogen-derived compounds. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.10.011

文献信息

• Steroidal quinols and their use for antioxidant therapy
  申请人：——

  公开号：US20030229060A1

  公开（公告）日：2003-12-11

  The present invention relates to novel estrogen-related steroidal quinols and their use as prodrugs for phenolic estrogens and estrogen analogs. The quinols of the present invention provide improved physicochemical properties, increased bioavailability, and improved distribution into tissues and penetration across the blood-brain barrier when compared to phenolic estrogens and estrogen analogs.

  本发明涉及新型雌激素相关的类固醇醌类化合物，以及它们作为酚类雌激素和雌激素类似物的前药的用途。与酚类雌激素和雌激素类似物相比，本发明的醌类化合物具有改善的物理化学性质、增加的生物利用度以及改善的组织分布和穿越血脑屏障能力。
• STEROIDAL QUINOLS AS PRODRUGS OF ANTIOXIDANTS
  申请人：University of Florida Research Foundation, Inc.

  公开号：EP1490392B1

  公开（公告）日：2007-02-14
• US7026306B2
  申请人：——

  公开号：US7026306B2

  公开（公告）日：2006-04-11
• Mechanistic investigations on the antioxidant action of a neuroprotective estrogen derivative
  作者：Katalin Prokai-Tatrai、Pal Perjesi、Nilka M. Rivera-Portalatin、James W. Simpkins、Laszlo Prokai

  DOI：10.1016/j.steroids.2007.10.011

  日期：2008.3

  Antioxidant action is an important component of the complex neuroprotective effect of estrogens. Combining theoretical prediction and subsequent experimental confirmation by chemical and in vitro paradigms, this study focused on the mechanistic aspects of hydroxyl radical scavenging by 17 beta-butoxy-1,3,5(10)-estratrien-3-ol, a synthetic derivative of 17 beta-estradiol with increased potency to inhibit lipid peroxidation and reduced affinity to estrogen-receptors compared to the endogenous hormone. In the process that acts as a "chemical shield," the phenolic A-ring turns into 10 beta-hydroxy-17 beta-butoxy-1,3,5(10)-estratrien-3-one, a non-aromatic paro-quinol, upon capturing hydroxyl radicals, which results in the complete loss of estrogen-receptor affinity and antioxidant activity. However, the parent compound is apparently recovered in brain tissue from this para-quinol via enzyme-catalyzed NAD(P)H-dependent reductive aromatization without causing oxidative stress. Taken together, our report argues for a previously unrecognized antioxidant cycle for estrogen-derived compounds. (C) 2007 Elsevier Inc. All rights reserved.