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

文献信息

• Discovery of Potent, Orally-Active, and Muscle-Selective Androgen Receptor Modulators Based on an <i>N</i>-Aryl-hydroxybicyclohydantoin Scaffold
  作者：Chongqing Sun、Jeffrey A. Robl、Tammy C. Wang、Yanting Huang、Joyce E. Kuhns、John A. Lupisella、Blake C. Beehler、Rajasree Golla、Paul G. Sleph、Ramakrishna Seethala、Aberra Fura、Stanley R. Krystek、Yongmi An、Mary F. Malley、John S. Sack、Mark E. Salvati、Gary J. Grover、Jacek Ostrowski、Lawrence G. Hamann

  DOI：10.1021/jm061101w

  日期：2006.12.1

  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.