2-chloro-4-[[(±)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-4-[[(±)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile
• 英文别名: 2-Chloro-4-[[2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile；2-chloro-4-[(2-hydroxy-2-methylcyclopentyl)amino]-3-methylbenzonitrile
• 化学式: C₁₄H₁₇ClN₂O
• 分子量: 264.755
• InChiKey: CXFSVKGROITHRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-4-[[(±)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile 生成 2-chloro-4-[[(1R,2R)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile
  参考文献：
  名称：

  2-Chloro-4-[[(1R,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile: A Transdermal Selective Androgen Receptor Modulator (SARM) for Muscle Atrophy

  摘要：

  A transdermal SARM has a potential to have therapeutic benefit through anabolic activity in muscle, while sparing undesired effects of benign prostate hyperplasia (BPH) and liver-mediated decrease in HDL-C. 2-Chloro-4-[(2-hydroxy-2-methyl-cyclopentyl)amino]-3-methyl-benzonitrile 6 showed the desired muscle and prostate effects in a preclinical ORX rat model. Compound 6 had minimal effect on HDL-C levels in cynomolgus monkeys and showed human cadaver skin permeability, thus making it an effective tool for proof of concept studies in a clinical setting.

  DOI：

  10.1021/acs.jmedchem.5b01168
• 作为产物：
  描述：

  1-甲基环戊烯 在 ammonium hydroxide 、 lithium carbonate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 52.0h， 生成 2-chloro-4-[[(±)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile
  参考文献：
  名称：

  2-Chloro-4-[[(1R,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile: A Transdermal Selective Androgen Receptor Modulator (SARM) for Muscle Atrophy

  摘要：

  A transdermal SARM has a potential to have therapeutic benefit through anabolic activity in muscle, while sparing undesired effects of benign prostate hyperplasia (BPH) and liver-mediated decrease in HDL-C. 2-Chloro-4-[(2-hydroxy-2-methyl-cyclopentyl)amino]-3-methyl-benzonitrile 6 showed the desired muscle and prostate effects in a preclinical ORX rat model. Compound 6 had minimal effect on HDL-C levels in cynomolgus monkeys and showed human cadaver skin permeability, thus making it an effective tool for proof of concept studies in a clinical setting.

  DOI：

  10.1021/acs.jmedchem.5b01168

文献信息

• [EN] SELECTIVE ANDROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS SÉLECTIFS D'UN RÉCEPTEUR DES ANDROGÈNES
  申请人：LILLY CO ELI

  公开号：WO2013055577A1

  公开（公告）日：2013-04-18

  The present invention provides novel selective androgen receptor modulators and their salts and pharmaceutical compositions thereof.

  本发明提供了新型选择性雄激素受体调节剂及其盐和药物组合物。
• 4-aminobenzonitrile selective androgen receptor modulators
  申请人：Eli Lilly and Company

  公开号：US08658693B2

  公开（公告）日：2014-02-25

  The present invention provides novel selective androgen receptor modulators and their salts and pharmaceutical compositions thereof.

  本发明提供了新型选择性雄激素受体调节剂及其盐和制药组合物。
• Selective Androgen Receptor Modulators
  申请人：Eli Lilly and Company

  公开号：US20130217762A1

  公开（公告）日：2013-08-22

  The present invention provides novel selective androgen receptor modulators and their salts and pharmaceutical compositions thereof.

  本发明提供了新型选择性雄激素受体调节剂及其盐和制药组合物。
• SELECTIVE ANDROGEN RECEPTOR MODULATORS
  申请人：Eli Lilly and Company

  公开号：EP2766350A1

  公开（公告）日：2014-08-20
• US8658693B2
  申请人：——

  公开号：US8658693B2

  公开（公告）日：2014-02-25