(±)-4-((3-methylpiperazin-1-yl)methyl)benzonitrile | 685536-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-4-((3-methylpiperazin-1-yl)methyl)benzonitrile
• 英文别名: 4-(3-methyl-piperazin-1-ylmethyl)-benzonitrile；4-[(3-methyl-1-piperazinyl)methyl]Benzonitrile；4-[(3-methylpiperazin-1-yl)methyl]benzonitrile
• CAS: 685536-08-7
• 化学式: C₁₃H₁₇N₃
• mdl: MFCD16038677
• 分子量: 215.298
• InChiKey: FJOMKZCZBVJOKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-chloropropyl)piperidine-4-carboxamide 、 (±)-4-((3-methylpiperazin-1-yl)methyl)benzonitrile 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以23%的产率得到(±)-1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-(4-(4-cyanobenzyl)-2-methylpiperazin-1-yl)propyl)piperidine-4-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists

  摘要：

  Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.052
• 作为产物：
  描述：

  2-甲基哌嗪 、 对氰基氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以82%的产率得到(±)-4-((3-methylpiperazin-1-yl)methyl)benzonitrile
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists

  摘要：

  Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.052

文献信息

• 1-(4-Benzyl-piperazin-1-yl)-3-phenyl-propenone derivatives
  申请人：Bollbuck Birgit

  公开号：US20060173004A1

  公开（公告）日：2006-08-03

  A compound of formula (I), or a pharmaceutically acceptable salt or ester thereof, wherein the symbols have meaning as defined, which are antagonists of CCR-1 and which find use pharmaceutically for treatment of diseases and conditions in which CCR-1 is implicated, e.g. inflammatory diseases.

  式(I)的化合物，或其药学上可接受的盐或酯，其中符号的含义如定义所示，它们是CCR-1的拮抗剂，并且在药学上用于治疗CCR-1参与的疾病和情况，例如炎症性疾病。
• 1-(4-BENZYL-PIPERAZIN-1-YL)-3-PHENYL-PROPENONE DERIVATIVES
  申请人：Novartis AG

  公开号：EP1558594A2

  公开（公告）日：2005-08-03
• US7645760B2
  申请人：——

  公开号：US7645760B2

  公开（公告）日：2010-01-12
• [EN] 1-(4-BENZYL-PIPERAZIN-1-YL)-3-PHENYL-PROPENONE DERIVATIVES<br/>[FR] DERIVES DE 1-(4-BENZYL-PIPERAZINE-1-YL)-3-PHENYL-PROPENONE
  申请人：NOVARTIS AG

  公开号：WO2004037796A2

  公开（公告）日：2004-05-06

  A compound of formula (I), or a pharmaceutically acceptable salt or ester thereof, wherein the symbols have meaning as defined, which are antagonists of CCR-1 and which find use pharmaceutically for treatment of diseases and conditions in which CCR-1 is implicated, e.g. inflammatory diseases.