VUF 5746

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: VUF 5746
• 英文别名: 4-(p-chlorophenyl)-1-(4-phenylbutyl)piperidin-4-ol；4-(4-Chlorophenyl)-4-hydroxy-1-(4-phenylbutyl)piperidine；VUF5746；4-(4-Chloro-phenyl)-1-(4-phenyl-butyl)-piperidin-4-ol；4-(4-chlorophenyl)-1-(4-phenylbutyl)piperidin-4-ol
• 化学式: C₂₁H₂₆ClNO
• 分子量: 343.897
• InChiKey: IYHFUJULQNQFMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苯基丁醇 在 四氯化碳 、 sodium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 VUF 5746
  参考文献：
  名称：

  Synthesis of N-ω-Phenylalkyl-4-(p-chlorophenyl)-piperidin-4-ol Analogues with Potent Antiproliferative Activity Against HCT-116 Cells

  摘要：

  Some opioid analogues, such as morphine and loperamide, were reported to exhibit weak antiproliferative activity against tumor cells. In a study of loperamide analogues, we found that adding an N-omega-phenylalkyl group onto the 4-arylpiperidin-4-ol unit can have important effects on the antiproliferative activity of such compounds against HCT-116 cells. We optimized the distance between the phenyl group and 4-arylpiperidin unit to promote such activity.

  DOI：

  10.3987/com-18-s(t)25

文献信息

• Synthesis and Structure−Activity Relationship of the First Nonpeptidergic Inverse Agonists for the Human Cytomegalovirus Encoded Chemokine Receptor US28
  作者：Janneke W. Hulshof、Paola Casarosa、Wiro M. P. B. Menge、Leena M. S. Kuusisto、Henk van der Goot、Martine J. Smit、Iwan J. P. de Esch、Rob Leurs

  DOI：10.1021/jm050418d

  日期：2005.10.1

  US28 is a human cytomegalovirus (HCMV) encoded G-protein-coupled receptor that signals in a constitutively active manner. Recently, we identified 1 5-(4-(4-chlorophenyl)-4-hydroxy-piperidin-1-yl)-2,2-diphenylpentanenitrile} as the first reported nonpeptidergic inverse agonist for a viral-encoded chemokine receptor. Interestingly, this compound is able to partially inhibit the viral entry of HIV-1. In this study we describe the synthesis of 1 and several of its analogues and unique structure-activity relationships for this first class of small-molecule ligands for the chemokine receptor US28. Moreover, the compounds have been pharmacologically characterized as inverse agonists on US28. By modification of lead structure 1, it is shown that a 4-phenylpiperidine moiety is essential for affinity and activity. Other structural features of 1 are shown to be of less importance. These compounds define the first SAR of ligands on a viral GPCR (US28) and may therefore serve as important tools to investigate the significance of US28-mediated constitutive activity during viral infection.
• US6124323
  申请人：——

  公开号：——

  公开（公告）日：——
• EP0869792A4
  申请人：——

  公开号：EP0869792A4

  公开（公告）日：1999-09-22
• 4-SUBSTITUTED PIPERIDINE ANALOGS AND THEIR USE AS SUBTYPE SELECTIVE NMDA RECEPTOR ANTAGONISTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0869792A2

  公开（公告）日：1998-10-14
• US6124323A
  申请人：——

  公开号：US6124323A

  公开（公告）日：2000-09-26