17β-butoxy-1,3,5(10)-estratrien-3-ol | 319427-05-9

• 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: 17β-butoxy-1,3,5(10)-estratrien-3-ol
• 英文别名: 17β-Butoxyestra-1,3,5(10)-trien-3-ol；(8R,9S,13S,14S,17S)-17-butoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS: 319427-05-9
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: LWWBVLTYABFIPB-AANPDWTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  雌二醇 在 palladium on activated charcoal ammonium formate 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.5h， 生成 17β-butoxy-1,3,5(10)-estratrien-3-ol
  参考文献：
  名称：

  17beta-烷氧基-1,3,5（10）-三烯作为潜在的抗氧化应激神经保护剂的合成和生物学评估。

  摘要：

  从3-O-苄基-17β-雌二醇与氢化钠/烷基卤化物获得雌二醇的17beta-O-烷基醚（甲基，乙基，丙基，丁基，己基和辛基），然后除去O-苄基保护基通过催化转移氢化。与雌二醇相比，由于暴露于谷氨酸而导致的神经（HT-22）细胞对氧化应激的保护作用增强是由较高的（C-3至C-8）烷基醚提供的，而甲基和乙基醚则明显降低了神经保护作用。封闭A环的酚羟基（3-OH）的亲脂性（丁基和辛基）醚没有活性。

  DOI：

  10.1021/jm000280t

文献信息

• Alkyl ether modified polycyclic compounds having a terminal phenol and uses for protection of cells
  申请人：——

  公开号：US20020035100A1

  公开（公告）日：2002-03-21

  Methods and compositions are provided for achieving a cytoprotective effect by selecting a polycyclic compound with a phenol group at one end of the molecule and a carbon ring at the other such that an alkyl ether functional group in which the alkyl group has a formula C n H 2n+1 (where n is at least 3 and less than 20) is positioned on the carbon ring. The compound may be used to achieve a cytoprotective effect in cells and to retard the development of a degenerative condition in a subject suffering from a disease, trauma or aging.

  本发明提供了一种通过选择具有分子一端带有酚基团，而另一端带有碳环的多环化合物，使得碳环上有一种烷基醚官能团，其中烷基的公式为CnH2n+1（其中n至少为3且小于20），以实现细胞保护效应的方法和组合物。该化合物可用于在细胞中实现细胞保护效应，并延缓患有疾病、创伤或衰老的受试者的退行性状况的发展。
• Synthesis and Biological Evaluation of 17β-Alkoxyestra-1,3,5(10)-trienes as Potential Neuroprotectants Against Oxidative Stress
  作者：Laszlo Prokai、Su-Min Oon、Katalin Prokai-Tatrai、Khalil A. Abboud、James W. Simpkins

  DOI：10.1021/jm000280t

  日期：2001.1.1

  17beta-O-Alkyl ethers (methyl, ethyl, propyl, butyl, hexyl, and octyl) of estradiol were obtained from 3-O-benzyl-17beta-estradiol with sodium hydride/alkyl halide, followed by the removal of the O-benzyl protecting group via catalytic transfer hydrogenation. An increase compared to estradiol in the protection of neural (HT-22) cells against oxidative stress due to exposure of glutamate was furnished

  从3-O-苄基-17β-雌二醇与氢化钠/烷基卤化物获得雌二醇的17beta-O-烷基醚（甲基，乙基，丙基，丁基，己基和辛基），然后除去O-苄基保护基通过催化转移氢化。与雌二醇相比，由于暴露于谷氨酸而导致的神经（HT-22）细胞对氧化应激的保护作用增强是由较高的（C-3至C-8）烷基醚提供的，而甲基和乙基醚则明显降低了神经保护作用。封闭A环的酚羟基（3-OH）的亲脂性（丁基和辛基）醚没有活性。
• 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.