(2S)-1-[[(4-nitro-1-naphthalenyl)amino]carbonyl]-2-pyrrolidinecarboxylic acid methyl ester | 496840-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-1-[[(4-nitro-1-naphthalenyl)amino]carbonyl]-2-pyrrolidinecarboxylic acid methyl ester
• 英文别名: methyl (2S)-1-[(4-nitronaphthalen-1-yl)carbamoyl]pyrrolidine-2-carboxylate
• CAS: 496840-99-4
• 化学式: C₁₇H₁₇N₃O₅
• 分子量: 343.339
• InChiKey: VSOALFJFROAJHB-HNNXBMFYSA-N

物化性质

• 沸点：
  587.1±50.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 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：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-1-[[(4-nitro-1-naphthalenyl)amino]carbonyl]-2-pyrrolidinecarboxylic acid methyl ester 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 tetrahydro-2-(4-nitro-1-naphthalenyl)-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-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：

  L-脯氨酸甲酯 、 1-异氰酸基-4-硝基萘 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 生成 (2S)-1-[[(4-nitro-1-naphthalenyl)amino]carbonyl]-2-pyrrolidinecarboxylic acid methyl ester
  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

• Bicyclic modulators of androgen receptor function
  申请人：——

  公开号：US20030055094A1

  公开（公告）日：2003-03-20

  The invention provides compounds of the formula I 1 wherein the substitutents are as described herein. Further provided are methods of using such compounds for the treatment of nuclear hormone receptor-associated conditions, such as age related diseases, for example sarcopenia, and also provided are pharmaceutical compositions containing such compounds.

  该发明提供了公式I1中的化合物，其中取代基如本说明所述。进一步提供了使用这些化合物治疗核激素受体相关疾病的方法，例如与年龄相关的疾病，例如肌少症，并且还提供了含有这些化合物的药物组合物。
• US6670386B2
  申请人：——

  公开号：US6670386B2

  公开（公告）日：2003-12-30
• US6992102B2
  申请人：——

  公开号：US6992102B2

  公开（公告）日：2006-01-31
• 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.