(2S,3R)-1-(4-Cyano-naphthalen-1-ylcarbamoyl)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester | 496841-10-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-1-(4-Cyano-naphthalen-1-ylcarbamoyl)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: (2S,3R)-1-(4-Cyano-naphthalen-1-ylcarbamoyl)-3-hydroxy-pyrrolidine-2carboxylic acid methyl ester；methyl (2S,3R)-1-[(4-cyanonaphthalen-1-yl)carbamoyl]-3-hydroxypyrrolidine-2-carboxylate
• CAS: 496841-10-2
• 化学式: C₁₈H₁₇N₃O₄
• 分子量: 339.351
• InChiKey: MNTACUQHRDILHV-CVEARBPZSA-N

物化性质

• 沸点：
  634.3±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-(4-Cyano-naphthalen-1-ylcarbamoyl)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以61.3 g的产率得到(7R,7aS)-4-(Tetrahydro-7-hydroxy-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-1-naphthalenecarbonitrile
  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：

  4-氨基-1-萘羧腈 在 4 A molecular sieve 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (2S,3R)-1-(4-Cyano-naphthalen-1-ylcarbamoyl)-3-hydroxy-pyrrolidine-2-carboxylic 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。
• OPEN-CHAIN PROLYL UREA-RELATED MODULATORS OF ANDROGEN RECEPTOR FUNCTION
  申请人：Hamann G. Lawrence

  公开号：US20080108691A1

  公开（公告）日：2008-05-08

  There are provided nuclear hormone receptor modulating compounds of formula I wherein R 1 , R 2 , R 3 , X, Y, n and G 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. Other embodiments are also disclosed.

  提供了具有I式的核激素受体调节化合物，其中R1、R2、R3、X、Y、n和G如本文所述。还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，如肌肉萎缩症，同时还提供了含有这些化合物的制药组合物。还公开了其他实施例。
• 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
• US7632858B2
  申请人：——

  公开号：US7632858B2

  公开（公告）日：2009-12-15