2-(2-(4-(双(4-氯苯基)甲基)哌嗪-1-基)乙氧基)乙醇 | 103508-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-(4-(双(4-氯苯基)甲基)哌嗪-1-基)乙氧基)乙醇
• 英文名称: 2-(2-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)ethoxy)ethanol
• 英文别名: 2-{2-[4-(4,4'-dichloro-benzhydryl)-piperazin-1-yl]-ethoxy}-ethanol；2-{2-[4-(4,4'-dichloro-benzhydryl)-piperazino]-ethoxy}-ethanol；2-{2-[4-(4,4'-Dichlor-benzhydryl)-piperazino]-aethoxy}-aethanol；1-(4,4'-Dichlor-benzhydryl)-4-<2-(2-hydroxy-ethoxy)-ethyl>-piperazin；2-[2-[4-[Bis(4-chlorophenyl)methyl]piperazin-1-yl]ethoxy]ethanol；2-[2-[4-[bis(4-chlorophenyl)methyl]piperazin-1-yl]ethoxy]ethanol
• CAS: 103508-78-7
• 化学式: C₂₁H₂₆Cl₂N₂O₂
• 分子量: 409.356
• InChiKey: RGDPDSUFMWIZNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(4-(双(4-氯苯基)甲基)哌嗪-1-基)乙氧基)乙醇 、 2-[2-(2-t-叔丁氧羰基-氨基乙氧基]乙氧基]乙基溴化物 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.67h， 生成 C₃₂H₄₇Cl₂N₃O₆
  参考文献：
  名称：

  Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection

  摘要：

  Recently, we reported that chlorcyclizine (CCZ, Rac-2), an over-the-counter antihistamine piperazine drug, possesses in vitro and in vivo activity against hepatitis C virus. Here, we describe structure activity relationship (SAR) efforts that resulted in the optimization of novel chlorcyclizine derivatives as anti-HCV agents. Several compounds exhibited EC50 values below 10 nM against HCV infection, cytotoxicity selectivity indices above 2000, and showed improved in vivo pharmacokinetic properties. The optimized molecules can serve as lead preclinical candidates for the treatment of hepatitis C virus infection and as probes to study hepatitis C virus pathogenesis and host virus interaction.

  DOI：

  10.1021/acs.jmedchem.5b00752
• 作为产物：
  描述：

  1-氯-4-[氯(4-氯苯基)甲基]苯 在 三乙胺 、 甲苯 作用下， 生成 2-(2-(4-(双(4-氯苯基)甲基)哌嗪-1-基)乙氧基)乙醇
  参考文献：
  名称：

  Morren et al., Industrie Chimique Belge, 1957, vol. 22, p. 409,416

  摘要：

  DOI：

文献信息

• [EN] PIPERIDINE AND PIPERAZINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS AND CANCER<br/>[FR] DÉRIVÉS PIPÉRIDINE ET PIPÉRAZINE ET LEUR UTILISATION POUR TRAITER LES INFECTIONS VIRALES ET LE CANCER
  申请人：US HEALTH

  公开号：WO2015080949A1

  公开（公告）日：2015-06-04

  Disclosed are compounds of formula (I) (formula I),as antiviral agents, antineoplastic agents, pharmaceutical compositions comprising such compounds, and a method of use of these compounds, wherein X and Y are independently CH or N, o is 0, 1 or 2, and E is absent or is (CR13 R14 )m, NH, or S, F is absent or is (CR15 R16 )n, C=O, or -SO2 -, G is absent or is (CR17 CR18 )r, H is absent or is C=O, or -SO2 - and R1, Ar1, Ar2 are as defined in the specification. These compounds are antiviral agents and are contemplated in the treatment of viral infections, for example, hepatitis C, or are antineoplastic agents.

  揭示了化合物的结构式（I）（式I），作为抗病毒剂、抗肿瘤剂，包括这些化合物的药物组合物，以及这些化合物的使用方法，其中X和Y分别为CH或N，o为0、1或2，E不存在或为（CR13 R14）m、NH或S，F不存在或为（CR15 R16）n、C=O或-SO2-，G不存在或为（CR17 CR18）r，H不存在或为C=O或-SO2-，R1、Ar1、Ar2如规范中所定义。这些化合物是抗病毒剂，可用于治疗病毒感染，例如丙型肝炎，或作为抗肿瘤剂。
• PIPERIDINE AND PIPERAZINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS AND CANCER
  申请人：The U.S.A. as represented by the Secretary, Department of Health and Human Services

  公开号：EP3074001A1

  公开（公告）日：2016-10-05
• Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection
  作者：Shanshan He、Jingbo Xiao、Andrés E. Dulcey、Billy Lin、Adam Rolt、Zongyi Hu、Xin Hu、Amy Q. Wang、Xin Xu、Noel Southall、Marc Ferrer、Wei Zheng、T. Jake Liang、Juan J. Marugan

  DOI：10.1021/acs.jmedchem.5b00752

  日期：2016.2.11

  Recently, we reported that chlorcyclizine (CCZ, Rac-2), an over-the-counter antihistamine piperazine drug, possesses in vitro and in vivo activity against hepatitis C virus. Here, we describe structure activity relationship (SAR) efforts that resulted in the optimization of novel chlorcyclizine derivatives as anti-HCV agents. Several compounds exhibited EC50 values below 10 nM against HCV infection, cytotoxicity selectivity indices above 2000, and showed improved in vivo pharmacokinetic properties. The optimized molecules can serve as lead preclinical candidates for the treatment of hepatitis C virus infection and as probes to study hepatitis C virus pathogenesis and host virus interaction.
• Morren et al., Industrie Chimique Belge, 1957, vol. 22, p. 409,416
  作者：Morren et al.

  DOI：——

  日期：——