N-benzyl-4-(4-phenylbutyl)piperidine | 161829-88-5

• 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: N-benzyl-4-(4-phenylbutyl)piperidine
• 英文别名: 1-Benzyl-4-(4-phenylbutyl)piperidine
• CAS: 161829-88-5
• 化学式: C₂₂H₂₉N
• 分子量: 307.479
• InChiKey: GRLLNFANWRLKDV-UHFFFAOYSA-N

物化性质

• 沸点：
  416.747±14.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.001±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-(4-phenylbutyl)piperidine 在 chromium(VI) oxide 、 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-Benzyl-4-(2-ethyl-4-phenethyl-2H-pyrazol-3-yl)-piperidine
  参考文献：
  名称：

  Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains

  摘要：

  Replacement of the flexible connecting chains between the piperidine moiety and an aromatic group in previous CCR5 antagonists with heterocycles, such as pyrazole and isoxazole, provided potent CCR5 antagonists with excellent anti-HIV-1 activity in vitro. SAR studies revealed optimal placement of an unsubstituted nitrogen atom in the heterocycle to be meta to the bond connected to the 4-position of piperidine. Truncation of a benzyl group to a phenyl group afforded compounds with dramatically improved oral bioavailability, albeit with reduced activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.004
• 作为产物：
  描述：

  4-苯基-1-丁基溴 在 硼烷 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 N-benzyl-4-(4-phenylbutyl)piperidine
  参考文献：
  名称：

  Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains

  摘要：

  Replacement of the flexible connecting chains between the piperidine moiety and an aromatic group in previous CCR5 antagonists with heterocycles, such as pyrazole and isoxazole, provided potent CCR5 antagonists with excellent anti-HIV-1 activity in vitro. SAR studies revealed optimal placement of an unsubstituted nitrogen atom in the heterocycle to be meta to the bond connected to the 4-position of piperidine. Truncation of a benzyl group to a phenyl group afforded compounds with dramatically improved oral bioavailability, albeit with reduced activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.004

文献信息

• EP0714292A4
  申请人：——

  公开号：EP0714292A4

  公开（公告）日：1996-10-09
• SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：Cambridge Neuroscience, Inc.

  公开号：EP0714292A1

  公开（公告）日：1996-06-05
• [EN] SIGMA RECEPTOR LIGANDS AND THE USE THEREOF<br/>[FR] LIGANDS DU RECEPTEUR SIGMA ET LEUR UTILISATION
  申请人：CAMBRIDGE NEUROSCIENCE, INCORPORATED

  公开号：WO1995000131A1

  公开（公告）日：1995-01-05

  (EN) The invention relates to methods for the treatment of central nervous system disorders, neurological disorders, gastrointestinal disorders, drug abuse, angina, migraine, hypertension and depression by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof.(FR) L'invention se rapporte à des procédés permettant de traiter des troubles du système nerveux central, des troubles neurologiques, des désordres gastro-intestinaux, l'abus de médicaments, l'angine, la migraine, l'hypertension et la dépression, en administrant une composition pharmaceutique comprenant une quantité efficace de certains ligands du récepteur sigma à un patient nécessitant un tel traitement. L'invention se rapporte en outre à des nouveaux ligands du récepteur sigma ayant un pouvoir élevé de fixation sur ledit récepteur et à leurs compositions pharmaceutiques.
• Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains
  作者：Dong-Ming Shen、Min Shu、Sander G. Mills、Kevin T. Chapman、Lorraine Malkowitz、Martin S. Springer、Sandra L. Gould、Julie A. DeMartino、Salvatore J. Siciliano、Gloria Y. Kwei、Anthony Carella、Gwen Carver、Karen Holmes、William A. Schleif、Renee Danzeisen、Daria Hazuda、Joseph Kessler、Janet Lineberger、Michael D. Miller、Emilio A. Emini

  DOI：10.1016/j.bmcl.2003.12.004

  日期：2004.2

  Replacement of the flexible connecting chains between the piperidine moiety and an aromatic group in previous CCR5 antagonists with heterocycles, such as pyrazole and isoxazole, provided potent CCR5 antagonists with excellent anti-HIV-1 activity in vitro. SAR studies revealed optimal placement of an unsubstituted nitrogen atom in the heterocycle to be meta to the bond connected to the 4-position of piperidine. Truncation of a benzyl group to a phenyl group afforded compounds with dramatically improved oral bioavailability, albeit with reduced activity. (C) 2004 Elsevier Ltd. All rights reserved.