methyl (2S,3S)-3-hydroxy-1-[(4-nitronaphthalen-1-yl)carbamoyl]pyrrolidine-2-carboxylate | 918344-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (2S,3S)-3-hydroxy-1-[(4-nitronaphthalen-1-yl)carbamoyl]pyrrolidine-2-carboxylate
• CAS: 918344-31-7
• 化学式: C₁₇H₁₇N₃O₆
• 分子量: 359.338
• InChiKey: RXEIUHYRANZSIN-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-3-hydroxy-1-[(4-nitronaphthalen-1-yl)carbamoyl]pyrrolidine-2-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 (7R,7aS)-7-hydroxy-2-(4-nitronaphthalen-1-yl)-5,6,7,7a-tetrahydropyrrolo[1,2-c]imidazole-1,3-dione
  参考文献：
  名称：

  Discovery of Potent, Orally-Active, and Muscle-Selective Androgen Receptor Modulators Based on an N-Aryl-hydroxybicyclohydantoin Scaffold

  摘要：

  A novel, N-aryl-bicyclohydantoin selective androgen receptor modulator scaffold was discovered through structure-guided modifications of androgen receptor antagonists. A prototype compound (7R,7aS)-10b from this series is a potent and highly tissue-selective agonist of the androgen receptor. After oral dosing in a rat atrophied levator ani muscle model, (7R,7aS)-10b demonstrated efficacy at restoring levator ani muscle mass to that of intact controls and exhibited >50-fold selectivity for muscle over prostate.

  DOI：

  10.1021/jm061101w
• 作为产物：
  描述：

  反-3-羟基-L-脯氨酸 在 盐酸 、 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 methyl (2S,3S)-3-hydroxy-1-[(4-nitronaphthalen-1-yl)carbamoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Discovery of Potent, Orally-Active, and Muscle-Selective Androgen Receptor Modulators Based on an N-Aryl-hydroxybicyclohydantoin Scaffold

  摘要：

  A novel, N-aryl-bicyclohydantoin selective androgen receptor modulator scaffold was discovered through structure-guided modifications of androgen receptor antagonists. A prototype compound (7R,7aS)-10b from this series is a potent and highly tissue-selective agonist of the androgen receptor. After oral dosing in a rat atrophied levator ani muscle model, (7R,7aS)-10b demonstrated efficacy at restoring levator ani muscle mass to that of intact controls and exhibited >50-fold selectivity for muscle over prostate.

  DOI：

  10.1021/jm061101w