1-oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoate | 864661-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoate
• 英文别名: (3-oxo-2,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-6-yl) benzoate
• CAS: 864661-59-6
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: URFYABVEHYCXHG-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±38.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoate 、 2-氯-4-碘-3-甲基苯甲腈 在 copper(l) iodide potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以21%的产率得到[(3aS,6R,6aR)-2-(3-chloro-4-cyano-2-methylphenyl)-3-oxo-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrol-6-yl] benzoate
  参考文献：
  名称：

  Discovery of Potent and Muscle Selective Androgen Receptor Modulators through Scaffold Modifications

  摘要：

  A novel series of imidazolin-2-ones were designed and synthesized as highly potent, orally active and muscle selective androgen receptor modulators (SARMs), with most of the compounds exhibiting low nM in vitro potency in androgen receptor (AR) binding and functional assays. Once daily oral treatment with the lead compound 11a (AR K-i = 0.9 nM, EC50 = 1.8 nM) for 14 days induced muscle growth with an ED50 of 0.09 mg/kg, providing approximately 50-fold selectivity over prostate growth in an orchidectomized rat model. Pharmacokinetic studies in rats demonstrated that the lead compound 11a had oral bioavailability of 65% and a plasma half-life of 5.5 h. On the basis of their preclinical profiles, the SARMs in this series are expected to provide beneficial anabolic effects on muscle with minimal androgenic effects on prostate tissue.

  DOI：

  10.1021/jm070312d
• 作为产物：
  描述：

  6-Oxobicyclo[3.2.0]heptan-2-yl benzoate 在 2,4,6-三甲基苯磺酰羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 1-oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoate 、 2-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate
  参考文献：
  名称：

  Novel bicyclic compounds as modulators of androgen receptor function and method

  摘要：

  本发明涉及公式I所示的双环化合物，包含这种化合物的药物组合物以及使用这种化合物治疗与雄激素受体相关的疾病的方法，例如与年龄相关的疾病，例如肌少症，其中R1、R2、R5、X和n在此处定义。

  公开号：

  US20070004717A1

文献信息

• Novel Bicyclic Compounds As Modulators of Androgen Receptor Function And Method
  申请人：Li J. James

  公开号：US20080096954A1

  公开（公告）日：2008-04-24

  There are disclosed bicyclic compounds according to formula I, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example sarcopenia, wherein R 1 , R 2 , R 5 , X and n are defined herein.

  公开了根据式I的双环化合物，含有这种化合物的药物组合物以及使用这种化合物治疗与雄激素受体相关的疾病的方法，例如年龄相关疾病，例如肌肉萎缩症，其中R1，R2，R5，X和n在此定义。
• Bicyclic compounds as modulators of androgen receptor function and method
  申请人：Bristol-Myers Squibb Company

  公开号：US07732480B2

  公开（公告）日：2010-06-08

  There are disclosed bicyclic compounds according to formula I, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example sarcopenia, wherein R1, R2, R5, X and n are defined herein.

  公开了一种按照式子I所示的双环化合物，其中包含这种化合物的药物组成和使用这种化合物治疗与雄激素受体相关的疾病的方法，例如与年龄相关的疾病，例如肌肉萎缩症，其中R1、R2、R5、X和n在此被定义。
• EP1722790A4
  申请人：——

  公开号：EP1722790A4

  公开（公告）日：2007-10-31
• NOVEL BICYCLIC COMPOUNDS AS MODULATORS OF ANDROGEN RECEPTOR FUNCTION AND METHOD
  申请人：Bristol-Myers Squibb Company

  公开号：EP1722790A2

  公开（公告）日：2006-11-22
• US7696241B2
  申请人：——

  公开号：US7696241B2

  公开（公告）日：2010-04-13