(2S,3aS,3bR,5aR,9aR,9bS,11aS)-2-(methoxymethyl)-6,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,9b,10,11-decahydroindeno[5,4-f]quinoline-1,7-dione | 1179423-78-9

• 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: (2S,3aS,3bR,5aR,9aR,9bS,11aS)-2-(methoxymethyl)-6,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,9b,10,11-decahydroindeno[5,4-f]quinoline-1,7-dione
• CAS: 1179423-78-9
• 化学式: C₂₁H₃₁NO₃
• 分子量: 345.482
• InChiKey: BJEOEXLZALCKKD-OCGUKARYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3aS,3bR,5aR,9aR,9bS,11aS)-2-(methoxymethyl)-6,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,9b,10,11-decahydroindeno[5,4-f]quinoline-1,7-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到16α-(methoxymethyl)-17β-hydroxy-4-methyl-4-aza-5α-androst-1-en-3-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 16-Substituted 4-Azasteroids as Tissue-Selective Androgen Receptor Modulators (SARMs)

  摘要：

  A novel series of 16-substiuted-4-azasteroids has been identified as potential tissue-selective androgen receptor modulators. These ligands display potent hAR binding and agonist activity, low virilizing potential,and good pharmacokinetic profiles in dogs. On the basis of its in vitro profile, 21 was evaluated in the OVX and ORX rat models and exhibited all osteoanabolic, tissue-selective profile.

  DOI：

  10.1021/jm900880r
• 作为产物：
  描述：

  (4aR,4bS,6aS,9aS,9bR,11aR)-1,4a,6a-trimethyl-4a,4b,5,6,6a,8,9,9a,9b,10,11,11a-dodecahydro-1H-indeno[5,4-f]quinoline-2,7-dione 、 氯甲基甲基醚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 、 正己烷 为溶剂， 以33%的产率得到(2S,3aS,3bR,5aR,9aR,9bS,11aS)-2-(methoxymethyl)-6,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,9b,10,11-decahydroindeno[5,4-f]quinoline-1,7-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 16-Substituted 4-Azasteroids as Tissue-Selective Androgen Receptor Modulators (SARMs)

  摘要：

  A novel series of 16-substiuted-4-azasteroids has been identified as potential tissue-selective androgen receptor modulators. These ligands display potent hAR binding and agonist activity, low virilizing potential,and good pharmacokinetic profiles in dogs. On the basis of its in vitro profile, 21 was evaluated in the OVX and ORX rat models and exhibited all osteoanabolic, tissue-selective profile.

  DOI：

  10.1021/jm900880r

文献信息

• Design, Synthesis, and Biological Evaluation of 16-Substituted 4-Azasteroids as Tissue-Selective Androgen Receptor Modulators (SARMs)
  作者：Helen J. Mitchell、William P. Dankulich、George D. Hartman、Thomayant Prueksaritanont、Azriel Schmidt、Robert L. Vogel、Chang Bai、Sheila McElwee-Witmer、Hai Z. Zhang、Fang Chen、Chih-Tai Leu、Donald B. Kimmel、William J. Ray、Pascale Nantermet、Michael A. Gentile、Mark E. Duggan、Robert S. Meissner

  DOI：10.1021/jm900880r

  日期：2009.8.13

  A novel series of 16-substiuted-4-azasteroids has been identified as potential tissue-selective androgen receptor modulators. These ligands display potent hAR binding and agonist activity, low virilizing potential,and good pharmacokinetic profiles in dogs. On the basis of its in vitro profile, 21 was evaluated in the OVX and ORX rat models and exhibited all osteoanabolic, tissue-selective profile.