6,6-bis-(4-fluorophenyl)-1-piperazin-1-yl-hexan-1-one | 667936-68-7

• 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: 6,6-bis-(4-fluorophenyl)-1-piperazin-1-yl-hexan-1-one
• 英文别名: 6,6-bis(4-fluorophenyl)-1-piperazin-1-ylhexan-1-one
• CAS: 667936-68-7
• 化学式: C₂₂H₂₆F₂N₂O
• 分子量: 372.458
• InChiKey: SXHGFKOVRIYWNF-UHFFFAOYSA-N

物化性质

• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6-bis-(4-fluorophenyl)-1-piperazin-1-yl-hexan-1-one 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-[[4-[6,6-Bis(4-fluorophenyl)hexyl]piperazin-1-yl]methyl]-2,6-dimethoxyphenol
  参考文献：
  名称：

  Structure–activity relationships of trimethoxybenzyl piperazine N-type calcium channel inhibitors

  摘要：

  We previously reported the small organic N-type calcium channel blocker NP078585 that while efficacious in animal models for pain, exhibited modest L-type calcium channel selectivity and substantial off-target inhibition against the hERG potassium channel. Structure-activity studies to optimize NP078585 preclinical properties resulted in compound 16, which maintained high potency for N-type calcium channel blockade, and possessed excellent selectivity over the hERG (similar to 120-fold) and L-type (similar to 3600-fold) channels. Compound 16 shows significant anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain and is also efficacious in the rat formalin model of inflammatory pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.054
• 作为产物：
  描述：

  4-[6,6-bis-(4-fluoro-phenyl)-hexanoyl]-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 6,6-bis-(4-fluorophenyl)-1-piperazin-1-yl-hexan-1-one
  参考文献：
  名称：

  Calcium channel inhibitors comprising benzhydril spaced from piperazine

  摘要：

  描述了某些替代哌嗪化合物，可用于改变钙通道活性。

  公开号：

  US06943168B2

文献信息

• Scaffold-based design and synthesis of potent N-type calcium channel blockers
  作者：Gerald W. Zamponi、Zhong-Ping Feng、Lingyun Zhang、Hossein Pajouhesh、Yanbing Ding、Francesco Belardetti、Hassan Pajouhesh、David Dolphin、Lester A. Mitscher、Terrance P. Snutch

  DOI：10.1016/j.bmcl.2009.09.008

  日期：2009.11

  The therapeutic agents flunarizine and lomerizine exhibit inhibitory activities against a variety of ion channels and neurotransmitter receptors. We have optimized their scaffolds to obtain more selective N-type calcium channel blockers. During this optimization, we discovered NP118809 and NP078585, two potent N-type calcium channel blockers which have good selectivity over L-type calcium channels. Upon intraperitoneal administration both compounds exhibit analgesic activity in a rodent model of inflammatory pain. NP118809 further exhibits a number of favorable preclinical characteristics as they relate to overall pharmacokinetics and minimal off-target activity including the hERG potassium channel. (C) 2009 Elsevier Ltd. All rights reserved.
• EP1611116A2
  申请人：——

  公开号：EP1611116A2

  公开（公告）日：2006-01-04
• US6943168B2
  申请人：——

  公开号：US6943168B2

  公开（公告）日：2005-09-13
• [EN] CALCIUM CHANNEL INHIBITORS COMPRISING BENZHYDRIL SPACED FROM PIPERAZINE<br/>[FR] INHIBITEURS DES CANAUX CALCIQUES COMPRENANT DU BENZHYDRYLE ESPACE DE LA PIPERAZINE
  申请人：NEUROMED TECH INC

  公开号：WO2004089922A2

  公开（公告）日：2004-10-21

  Certain piperazine substituted compounds are described which are useful in altering calcium channel activity.