3-hydroxy-4-(1-methylpropyl)estra-1,3,5(10)-trien-17-one | 177353-06-9

• 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: 3-hydroxy-4-(1-methylpropyl)estra-1,3,5(10)-trien-17-one
• 英文别名: (8R,9S,13S,14S)-4-butan-2-yl-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 177353-06-9
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: RAZWPBMUHAHAMO-ICLNFKDNSA-N

物化性质

• 沸点：
  464.0±45.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-(1-methylpropyl)estra-1,3,5(10)-trien-17-one 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 乙醇 、 正戊烷 为溶剂， 生成 (8R,9S,13S,14S,17S)-4-sec-Butyl-2-tert-butyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  In vitro antioxidant effects of estrogens with a hindered 3-OH function on the copper-induced oxidation of low density lipoprotein

  摘要：

  Estrogens with some bulky alkyl substituents in both the 2- and 4-positions have been synthesized and evaluated for the ability to inhibit the in vitro oxidation of low density lipoprotein as determined by the thiobarbituric reactive substances method. The present compounds with bulky groups in either the 2- or the 4-position (but not both the 2- and 4-) were especially effective as antioxidants, having IC50 values lower than either estradiol or probucol; however, they do not bind to the estrogen receptor with any great affinities (RBA < 0.1 versus estradiol). This separation of antioxidant efficacy from estrogenicity may allow these compounds to serve as useful probes for ascertaining the relative importance of these effects in the cardioprotective role played by estrogens.

  DOI：

  10.1016/0039-128x(95)00234-h
• 作为产物：
  描述：

  3-hydroxy-4-(1'-methyl-1-propenyl)-estra-1,3,5(10)-trien-17-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以89%的产率得到3-hydroxy-4-(1-methylpropyl)estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  In vitro antioxidant effects of estrogens with a hindered 3-OH function on the copper-induced oxidation of low density lipoprotein

  摘要：

  Estrogens with some bulky alkyl substituents in both the 2- and 4-positions have been synthesized and evaluated for the ability to inhibit the in vitro oxidation of low density lipoprotein as determined by the thiobarbituric reactive substances method. The present compounds with bulky groups in either the 2- or the 4-position (but not both the 2- and 4-) were especially effective as antioxidants, having IC50 values lower than either estradiol or probucol; however, they do not bind to the estrogen receptor with any great affinities (RBA < 0.1 versus estradiol). This separation of antioxidant efficacy from estrogenicity may allow these compounds to serve as useful probes for ascertaining the relative importance of these effects in the cardioprotective role played by estrogens.

  DOI：

  10.1016/0039-128x(95)00234-h

文献信息

• Modified, hydroxy-substituted aromatic structures having cytoprotective activity
  申请人：Covey Douglas F.

  公开号：US09156876B2

  公开（公告）日：2015-10-13

  The present invention is directed to a process for conferring cytoprotection on a population of cells which comprises administering to that population of cells a compound comprising a hydroxy-substituted aromatic ring structure and a non-fused polycyclic, hydrophobic substituent attached thereto. In particular, the present invention is directed to such a process wherein the administered compound is phenolic, such as a steriod (e.g., estrogen), and has a non-fused polycyclic, hydrophobic substituent attached to the hydroxy-substituted A-ring thereof.

  本发明涉及一种为细胞群体提供细胞保护作用的过程，包括向该细胞群体施用一种包含一个氢氧基取代芳环结构和一个与之相连的非融合多环疏水取代基的化合物。具体来说，本发明涉及一种这样的过程，其中所施用的化合物是酚类的，例如类固醇（例如雌激素），并且具有一个与其氢氧基取代A环相连接的非融合多环疏水取代基。
• MODIFIED, HYDROXY-SUBSTITUTED AROMATIC STRUCTURES HAVING CYTOPROTECTIVE ACTIVITY
  申请人：Covey F. Douglas

  公开号：US20060009438A2

  公开（公告）日：2006-01-12

  Abstract of the Disclosure The present invention is directed to a process for conferring cytoprotection on a population of cells which comprises administering to that population of cells a compound comprising a hydroxy-substituted aromatic ring structure and a non-fused polycyclic, hydrophobic substituent attached thereto. In particular, the present invention is directed to such a process wherein the administered compound is phenolic, such as a steriod (e.g., estrogen), and has a non-fused polycyclic, hydrophobic substituent attached to the hydroxy-substituted A-ring thereof.

  本发明涉及一种用于给细胞群体提供细胞保护的方法，该方法包括向该细胞群体中投与一种化合物，所述化合物包含一个羟基取代的芳香环结构和一个附着于其上的非融合多环、疏水取代基。特别地，本发明涉及一种这样的方法，其中所投与的化合物为酚类，例如类固醇（例如雌激素），并且具有附着于其羟基取代的A环上的非融合多环、疏水取代基。
• Tert-butyl-substituted aromatic steroids having cytoprotective activity
  申请人：Washington University

  公开号：EP1834959A2

  公开（公告）日：2007-09-19

  The present invention is directed to modified, hydroxy-bearing aromatic ring structures having cytoprotective activity. More specifically, in a first embodiment the present invention is directed to phenolic compounds, and in particular steriods (eg., estrogens), hydrophobic substituent is attached to the hydroxy-substituted A-ring thereof. The present invention is further directed to a process for conferring cytoprotection to a population of cells involving the administration of the compound.

  本发明涉及具有细胞保护活性的经修饰的含羟基芳环结构。更具体地说，在第一个实施方案中，本发明涉及酚类化合物，特别是类固醇（如雌激素），疏水取代基连接到其羟基取代的 A 环上。本发明还进一步涉及一种对细胞群赋予细胞保护作用的工艺，该工艺涉及给药该化合物。
• US6844456B2
  申请人：——

  公开号：US6844456B2

  公开（公告）日：2005-01-18
• US9156876B2
  申请人：——

  公开号：US9156876B2

  公开（公告）日：2015-10-13