1-(3-(9H-Carbazol-9-yl)-1-propyl)-4-(4-chlorophenyl)piperidin-4-ol | 184845-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-(9H-Carbazol-9-yl)-1-propyl)-4-(4-chlorophenyl)piperidin-4-ol
• 英文别名: 4-Piperidinol, 1-[3-(9H-carbazol-9-yl)propyl]-4-(4-chlorophenyl)-；1-(3-carbazol-9-ylpropyl)-4-(4-chlorophenyl)piperidin-4-ol
• CAS: 184845-45-2
• 化学式: C₂₆H₂₇ClN₂O
• 分子量: 418.966
• InChiKey: YYPDZVKNBKQLKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  28.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(4-氯苯基)-4-羟基哌啶 、 9-(3-氯丙基)-9H-咔唑 在 sodium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以75%的产率得到1-(3-(9H-Carbazol-9-yl)-1-propyl)-4-(4-chlorophenyl)piperidin-4-ol
  参考文献：
  名称：

  Synthesis and pharmacological characterization of novel inverse agonists acting on the viral-encoded chemokine receptor US28

  摘要：

  G-protein coupled receptors encoded by viruses represent an unexplored class of potential drug targets. In this study, we describe the synthesis and pharmacological characterization of the first class of inverse agonists acting on the HCMV-encoded receptor US28. It is shown that replacement of the 4-hydroxy group of lead compound I with a methylamine group results in a significant 6-fold increase in affinity. Interestingly, increasing the rigidity of the spacer by the introduction of a double bond also leads to a significant increase in binding affinity compared to 1. These novel inverse agonists serve as valuable tools to elucidate the role of constitutive signaling in the pathogenesis of viral infection and may have therapeutic potential as leads for new antiviral drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.054

文献信息

• NOVEL HETEROCYCLIC CHEMISTRY
  申请人：NOVO NORDISK A/S

  公开号：EP0823905A1

  公开（公告）日：1998-02-18
• US6071932A
  申请人：——

  公开号：US6071932A

  公开（公告）日：2000-06-06
• [EN] NOVEL HETEROCYCLIC CHEMISTRY<br/>[FR] NOUVELLE CHIMIE HETEROCYCLIQUE
  申请人：NOVO NORDISK A/S

  公开号：WO1996034863A1

  公开（公告）日：1996-11-07

  (EN) A compound of formula (I). The present invention relates to therapeutically active carbazole derivatives, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating a central nervous system ailment related to the inhibition of GABA uptake via the GAT-4 subtype carrier.(FR) Composé de formule (I). Cette invention concerne des dérivés de carbazole thérapeutiquement actifs, un procédé de préparation de ces dérivés ainsi que des compositions pharmaceutiques comprenant ces composés. On utilise ces nouveaux composés dans le traitement d'un touble du système nerveux central lié à l'inhibition de l'apport du GABA par l'intermédiaire du vecteur du sous-type GAT-4.
• Synthesis and pharmacological characterization of novel inverse agonists acting on the viral-encoded chemokine receptor US28
  作者：Janneke W. Hulshof、Henry F. Vischer、Mark H.P. Verheij、Silvina A. Fratantoni、Martine J. Smit、Iwan J.P. de Esch、Rob Leurs

  DOI：10.1016/j.bmc.2006.06.054

  日期：2006.11

  G-protein coupled receptors encoded by viruses represent an unexplored class of potential drug targets. In this study, we describe the synthesis and pharmacological characterization of the first class of inverse agonists acting on the HCMV-encoded receptor US28. It is shown that replacement of the 4-hydroxy group of lead compound I with a methylamine group results in a significant 6-fold increase in affinity. Interestingly, increasing the rigidity of the spacer by the introduction of a double bond also leads to a significant increase in binding affinity compared to 1. These novel inverse agonists serve as valuable tools to elucidate the role of constitutive signaling in the pathogenesis of viral infection and may have therapeutic potential as leads for new antiviral drugs. (c) 2006 Elsevier Ltd. All rights reserved.