(S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (1-phenethyl-3-phenyl-propyl)-amide | 409366-80-9

• 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: (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (1-phenethyl-3-phenyl-propyl)-amide
• 英文别名: (2S)-1-(3,3-Dimethyl-1,2-dioxopentyl)-N-[3-phenyl-1-(2-phenylethyl)propyl]-2-pyrrolidinecarboxamide；(2S)-1-(3,3-dimethyl-2-oxopentanoyl)-N-(1,5-diphenylpentan-3-yl)pyrrolidine-2-carboxamide
• CAS: 409366-80-9
• 化学式: C₂₉H₃₈N₂O₃
• 分子量: 462.632
• InChiKey: XVLMZQQYJLIZTP-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S)-1-(1,2-二氧代-3,3-二甲基戊基)-2-吡咯烷甲酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (1-phenethyl-3-phenyl-propyl)-amide
  参考文献：
  名称：

  Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects

  摘要：

  The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.

  DOI：

  10.1021/jm010556c