(S)-3-环己基1-(3,3-二甲基-2-氧代戊酰基)哌啶-2-羧酸丙酯 | 152754-34-2

• 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
• 中文名称: (S)-3-环己基1-(3,3-二甲基-2-氧代戊酰基)哌啶-2-羧酸丙酯
• 英文名称: 3-cyclohexyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate
• 英文别名: 3-cyclohexylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)hexahydro-2-pyridinecarboxylate；(S)-3-Cyclohexylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate；3-cyclohexylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
• CAS: 152754-34-2
• 化学式: C₂₂H₃₇NO₄
• 分子量: 379.54
• InChiKey: NSEWQAAURSWQID-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  magnesium,2-methylbutane,chloride 在 4-二甲氨基吡啶 、 lithium hydroxide 、 D(+)-10-樟脑磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (S)-3-环己基1-(3,3-二甲基-2-氧代戊酰基)哌啶-2-羧酸丙酯
  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

• PIPECOLIC ACID DERIVATIVES FOR VISION AND MEMORY DISORDERS
  申请人：GPI NIL Holdings, Inc.

  公开号：EP1109554A2

  公开（公告）日：2001-06-27
• JP2002522485A
  申请人：——

  公开号：JP2002522485A

  公开（公告）日：2002-07-23
• US6376517B1
  申请人：——

  公开号：US6376517B1

  公开（公告）日：2002-04-23
• [EN] PIPECOLIC ACID DERIVATIVES FOR VISION AND MEMORY DISORDERS<br/>[FR] DERIVES DE L'ACIDE PIPECOLIQUE DESTINES AUX TROUBLES DE LA VISION ET DE LA MEMOIRE
  申请人：GUILFORD PHARM INC

  公开号：WO2000009109A2

  公开（公告）日：2000-02-24

  This invention relates to pharmaceutical compositions and methods for treating a vision disorder, improving vision, treating memory impairment, or enhancing memory performance using pipecolic acid derivatives, which have affinity for an FKBB-type (FKBP-12) immunophilin. The compounds may be immunosuppressive or non-immunosuppressive and are, for example, rapamycin, FK-506, Rap-Pa, way-124,666, SLB-506, GPI-1046, GPI-1044, GPI-1102, GPI-1116 or GPI-1206.
• Design, synthesis, and kinetic evaluation of high-affinity FKBP ligands and the X-ray crystal structures of their complexes with FKBP12
  作者：Dennis A. Holt、Juan I. Luengo、Dennis S. Yamashita、Hye Ja Oh、Arda L. Konialian、Hwa Kwo Yen、Leonard W. Rozamus、Martin Brandt、Mary J. Bossard、Mark A. Levy、Drake S. Eggleston、Jun Liang、L. Wayne Schultz、Thomas J. Stout、Jon Clardy

  DOI：10.1021/ja00075a008

  日期：1993.11.1

  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.