(1R)-1,3-diphenyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R)-1,3-diphenyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate
• 英文别名: (1R)-1,3-diphenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)hexahydro-2-pyridinecarboxylate；1,3-Diphenyl-1-propyl-1-(3,3-dimethyl-1,2-dioxypentyl)-2-piperidine carboxylate；[(1R)-1,3-diphenylpropyl] (2S)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
• 化学式: C₂₈H₃₅NO₄
• 分子量: 449.59
• InChiKey: WQTIHJORCCUQBO-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ω-苄基苯乙酮 在 4-二甲氨基吡啶 、 (+)-β-chlorodiisopinocampheylborane 、 二乙醇胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1R)-1,3-diphenyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate
  参考文献：
  名称：

  Design, synthesis, and kinetic evaluation of high-affinity FKBP ligands and the X-ray crystal structures of their complexes with FKBP12

  摘要：

  The design and synthesis of high-affinity FKBP12 ligands is described. These compounds potently inhibit the cis-trans-peptidylprolyl isomerase (rotamase) activity catalyzed by FKBP12 with inhibition constants (K(i,app)) as low as 1 nM, yet they possess remarkable structural simplicity relative to FK506 and rapamycin, from which they are conceptually derived. The atomic structures of three FKBP12-ligand complexes and of one unbound ligand were determined by X-ray crystallography and are compared to the FKBP12-FK506 and FKBP12-rapamycin complexes.

  DOI：

  10.1021/ja00075a008

文献信息

• INHIBITORS OF ROTAMASE ENZYME ACTIVITY
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：EP0777478B1

  公开（公告）日：2001-11-07
• NEUROPHILIN LIGANDS FOR TREATING OCULAR CONDITIONS
  申请人：Alcon, Inc.

  公开号：EP1227859B1

  公开（公告）日：2006-08-09
• US6187784B1
  申请人：——

  公开号：US6187784B1

  公开（公告）日：2001-02-13