3-(4-iodophenyl)-1-[(2S)-2-(4-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]propan-1-one | 1252038-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-iodophenyl)-1-[(2S)-2-(4-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]propan-1-one
• 英文别名: 3-(4-iodophenyl)-1-[(2S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]propan-1-one
• CAS: 1252038-08-6
• 化学式: C₂₂H₂₂IN₃O
• 分子量: 471.341
• InChiKey: IPMXVRBLSDBUMD-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-iodophenyl)-1-[(2S)-2-(4-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]propan-1-one 、 3-氨基苯硼酸 在 1,1'-bis(di-t-butylphosphino)ferrocene palladium dichloride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(3'-aminobiphenyl-4-yl)-1-[(2S)-2-(4-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]propan-1-one
  参考文献：
  名称：

  Design and Synthesis of Prolylcarboxypeptidase (PrCP) Inhibitors To Validate PrCP As A Potential Target for Obesity

  摘要：

  Prolycarboxypeptidase (PrCP) is a serine protease that may have a role in metabolism regulation. A class of reversible, potent, and selective PrCP inhibitors was developed starting from a mechanism based design for inhibiting this serine protease. Compound 8o inhibits human and mouse PrCP at IC(50) values of 1 and 2 nM and is not active (IC(50) > 25 mu M) against a panel of closely related proteases. It has lower serum binding than its close analogues and is bioavailable in mouse. Subchronic dosing of 8o in PrCP and WT mice at 100 mg/kg for 5 days resulted in a 5% reduction in body weight in WT mice and a reduction in PrCP KO mice.

  DOI：

  10.1021/jm101013m
• 作为产物：
  描述：

  (S)-5-phenyl-2-(pyrrolidin-2-yl)-1H-imidazole hydrochloride 、 3-(4-碘苯基)丙酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以2.17 g的产率得到3-(4-iodophenyl)-1-[(2S)-2-(4-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]propan-1-one
  参考文献：
  名称：

  Design and Synthesis of Prolylcarboxypeptidase (PrCP) Inhibitors To Validate PrCP As A Potential Target for Obesity

  摘要：

  Prolycarboxypeptidase (PrCP) is a serine protease that may have a role in metabolism regulation. A class of reversible, potent, and selective PrCP inhibitors was developed starting from a mechanism based design for inhibiting this serine protease. Compound 8o inhibits human and mouse PrCP at IC(50) values of 1 and 2 nM and is not active (IC(50) > 25 mu M) against a panel of closely related proteases. It has lower serum binding than its close analogues and is bioavailable in mouse. Subchronic dosing of 8o in PrCP and WT mice at 100 mg/kg for 5 days resulted in a 5% reduction in body weight in WT mice and a reduction in PrCP KO mice.

  DOI：

  10.1021/jm101013m