N,N'-双[(4-甲氧基苯基)甲基]丁烷-1,4-二胺 | 218956-13-9

• 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: N,N'-双[(4-甲氧基苯基)甲基]丁烷-1,4-二胺
• 英文名称: N1,N4-bis(4-methoxybenzyl)butane-1,4-diamine
• 英文别名: N~1~,N~4~-Bis[(4-methoxyphenyl)methyl]butane-1,4-diamine；N,N'-bis[(4-methoxyphenyl)methyl]butane-1,4-diamine
• CAS: 218956-13-9
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: RLBUJFLNOYOSCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.3±40.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  原甲酸三乙酯 、 N,N'-双[(4-甲氧基苯基)甲基]丁烷-1,4-二胺 在 氯化铵 作用下， 反应 18.0h， 以79%的产率得到1,3-bis(p-methoxybenzyl)-4,5,6,7-tetrahydro-1,3-diazepinium chloride
  参考文献：
  名称：

  Palladium-Catalyzed Suzuki-Miyaura Reaction of Aryl Chlorides in Aqueous Media Using Tetrahydrodiazepinium Salts as Carbene Ligands

  摘要：

  开发了一种高效、易于操作且对环境无害的钯介导Suzuki交叉偶联反应工艺。原位制备的三组分体系Pd(OAc)2、1,3-二烷基四氢二氮杂萘氯盐（2a-e）和K2CO3能够定量催化不活泼芳香氯的Suzuki-Miyaura交叉偶联反应。

  DOI：

  10.1055/s-2005-872673
• 作为产物：
  描述：

  N,N'-1,4-Tetramethylenebis[p-methoxybenzylidenealdimine] 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 N,N'-双[(4-甲氧基苯基)甲基]丁烷-1,4-二胺
  参考文献：
  名称：

  一系列N，N'-取代的二胺的合成及其抗动素体活性

  摘要：

  通过将游离的脂肪族二胺与不同的取代的苯甲醛进行受控的还原胺化反应，制备了一系列25个N，N'-取代的二胺。体外筛选该文库对人类非洲锥虫病，恰加斯氏病和内脏利什曼病的病原体的抗寄生虫活性。最有效的化合物衍生自包含4-OBn取代的亚二胺子集，在亚微摩尔（针对锥虫锥）或纳摩尔（针对布鲁氏锥虫和利什曼原虫donovani）范围内具有50％的寄生虫生长抑制作用。我们得出的结论是，该系列N，N'-取代的二胺成员提供了新的铅结构，这些结构具有治疗锥虫和利什曼病的潜力。

  DOI：

  10.1016/j.bmcl.2011.12.101

文献信息

• Synthesis and antikinetoplastid activity of a series of N,N′-substituted diamines
  作者：Andrea P. Caminos、Esteban A. Panozzo-Zenere、Shane R. Wilkinson、Babu L. Tekwani、Guillermo R. Labadie

  DOI：10.1016/j.bmcl.2011.12.101

  日期：2012.2

  A series of 25 N,N′-substituted diamines were prepared by controlled reductive amination of free aliphatic diamines with different substituted benzaldehydes. The library was screened in vitro for antiparasitic activity on the causative agents of human African trypanosomiasis, Chagas’ disease and visceral leishmaniasis. The most potent compounds were derived from a subset of diamines that contained

  通过将游离的脂肪族二胺与不同的取代的苯甲醛进行受控的还原胺化反应，制备了一系列25个N，N'-取代的二胺。体外筛选该文库对人类非洲锥虫病，恰加斯氏病和内脏利什曼病的病原体的抗寄生虫活性。最有效的化合物衍生自包含4-OBn取代的亚二胺子集，在亚微摩尔（针对锥虫锥）或纳摩尔（针对布鲁氏锥虫和利什曼原虫donovani）范围内具有50％的寄生虫生长抑制作用。我们得出的结论是，该系列N，N'-取代的二胺成员提供了新的铅结构，这些结构具有治疗锥虫和利什曼病的潜力。
• Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors
  作者：Jong Yeon Hwang、Hee-Young Kim、Suyeon Jo、Eunjung Park、Jihyun Choi、Sunju Kong、Dong-Sik Park、Ja Myung Heo、Jong Seok Lee、Yoonae Ko、Inhee Choi、Jonathan Cechetto、Jaeseung Kim、Jinhwa Lee、Zaesung No、Marc Peter Windisch

  DOI：10.1016/j.ejmech.2013.09.055

  日期：2013.12

  In order to identify novel anti-hepatitis C virus (HCV) agents we devised cell-based strategies and screened phenotypically small molecule chemical libraries with infectious HCV particles, and identified a hit compound (1) containing a hexahydropyrimidine (HHP) core. During our cell-based SAR study, we observed a conversion of HHP 1 into a linear diamine (6), which is the active component in inhibiting HCV and exhibited comparable antiviral activity to the cyclic HHP I. In addition, we engaged into the biological characterization of HHP and demonstrated that HHP does not interfere with HCV RNA replication, but with entry and release of viral particles. Here we report the results of the preliminary SAR and mechanism of action studies with HHP. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Induction of apoptosis by aryl-substituted diamines: role of aromatic group substituents and distance between nitrogens
  作者：Mark R Burns、Solveig LaTurner、Josh Ziemer、Maralee McVean、Bruce Devens、C.Lance Carlson、Gerard F Graminski、Scott M Vanderwerf、Reitha S Weeks、Jay Carreon

  DOI：10.1016/s0960-894x(02)00156-7

  日期：2002.5

  A series of aromatic substituted diamines was synthesized and characterized for their cytotoxic profiles against human breast and prostate tumor cell lines. Following a structure function analysis of the effects of changes of the benzyl substituents and the distance between amino groups the most potent analogues were analyzed biologically and were shown to induce apoptosis. These compounds do not induce the enzyme SSAT or deplete intracellular polyamine levels, mechanisms demonstrated by other cytotoxic polyamine analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.
• SPIROCYCLE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：Lundbeck La Jolla Research Center, Inc.

  公开号：EP3455226B1

  公开（公告）日：2020-12-30
• A minimalistic approach to develop new anti-apicomplexa polyamines analogs
  作者：Esteban A. Panozzo-Zénere、Exequiel O.J. Porta、Gustavo Arrizabalaga、Lucía Fargnoli、Shabana I. Khan、Babu L. Tekwani、Guillermo R. Labadie

  DOI：10.1016/j.ejmech.2017.11.069

  日期：2018.1

  The development of new chemical entities against the major diseases caused by parasites is highly desired. A library of thirty diamines analogs following a minimalist approach and supported by chemoinformatics tools have been prepared and evaluated against apicomplexan parasites. Different member of the series of N,N′-disubstituted aliphatic diamines shown in vitro activities at submicromolar concentrations

  迫切需要开发新的化学实体来对抗寄生虫引起的主要疾病。遵循极简主义方法并在化学信息学工具的支持下，已经制备了 30 个二胺类似物的文库，并针对 apicomplexan 寄生虫进行了评估。 N , N'-二取代脂肪族二胺系列的不同成员在亚微摩尔浓度下表现出体外活性，并且对弓形虫以及对氯喹敏感和耐药的恶性疟原虫菌株具有高选择性。为了证明仲胺的重要性，合成了十种N ， N ， N '， N'-四取代的脂肪族二胺衍生物，其活性比它们的二取代对应物低得多。进行理论研究以确定控制化合物活性的电子因素。