(21S)-1-aza-4,4-dimethyl-6,19-dioxa-2,3,7,20-tetraoxobicyclo<19.4.0>pentacosane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: (21S)-1-aza-4,4-dimethyl-6,19-dioxa-2,3,7,20-tetraoxobicyclo<19.4.0>pentacosane
• 英文别名: (21S)-1Aza-4,4-dimethyl-6,19-dioxa-2,3,7,20-tetraoxobicyclo[19.4.0] pentacosane；(21S)-4,4-dimethyl-6,19-dioxa-1-azabicyclo[19.4.0]pentacosane-2,3,7,20-tetrone
• 化学式: C₂₄H₃₉NO₆
• 分子量: 437.577
• InChiKey: VUCSBBBCFXBFFY-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  12-羟基十二酸 在 4-二甲氨基吡啶 、 三氯化铝 、 D(+)-10-樟脑磺酸 、 potassium hydrogencarbonate 、 N,N-二甲基苯胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 67.0h， 生成 (21S)-1-aza-4,4-dimethyl-6,19-dioxa-2,3,7,20-tetraoxobicyclo<19.4.0>pentacosane
  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 derivative hair growth compositions and uses
  申请人：GPI NIL Holdings, Inc.

  公开号：US20010036947A1

  公开（公告）日：2001-11-01

  This invention relates to pharmaceutical compositions and methods for treating alopecia and promoting hair growth using pipecolic acid derivatives.

  本发明涉及使用哌啶醇酸衍生物治疗脱发和促进毛发生长的药物组合物和方法。
• 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
• 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.