N,N'-bis-(3-benzylaminopropyl)butane-1,4-diamine | 119493-76-4

• 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: N,N'-bis-(3-benzylaminopropyl)butane-1,4-diamine
• 英文别名: N¹,N¹²-dibenzylspermine；DBSPM；1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane；n,n'-Bis[3-(benzylamino)propyl]butane-1,4-diamine
• CAS: 119493-76-4
• 化学式: C₂₄H₃₈N₄
• 分子量: 382.593
• InChiKey: CNCQKPGLZYJPGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  精胺 在 sodium tetrahydroborate 作用下， 以 苯 为溶剂， 生成 N,N'-bis-(3-benzylaminopropyl)butane-1,4-diamine
  参考文献：
  名称：

  SUR QUELQUES DÉRIVÉS PHOSPHORES DE LA SPERMINE

  摘要：

  摘要 精胺与芳香醛的反应导致双亚胺 1' 型和六氢嘧啶 1 型之间的平衡体系。相反，精胺的甲醛加合物仅存在于六氢嘧啶 9 型上。1-1' 很容易被 HCl 水解随着醛和精胺的再生。NaBH4，1-1' 的还原导致二苄基精胺 8 和膦酸加合物 2 或 6 从 1-1' 和膦酸氢盐获得。最后两个反应以 9 失败。相反，9 和 1-1' 与四甲基氯二氧杂磷杂环戊烷反应良好，形成环亚膦酰胺 10 和 5。在第二种情况下，可以通过 31P NMR 观察到动力学中间体 3。

  DOI：

  10.1080/10426509608037952

文献信息

• Novel polyamine derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0277635A2

  公开（公告）日：1988-08-10

  This invention relates to certain polyamine deriva­tives, to the methods and intermediates useful for their preparation, and to their use in treating diseases caused by infestation with a variety of parasitic protozoa.

  本发明涉及某些多胺衍生物、用于制备多胺衍生物的方法和中间体，以及多胺衍生物在治疗由多种寄生原虫感染引起的疾病中的用途。
• Polyamine derivatives as inhibitors of trypanothione reductase and assessment of their trypanocidal activities
  作者：Mary C. O'Sullivan、Qibing Zhou、Zhili Li、Timothy B. Durham、Donna Rattendi、Schennella Lane、Cyrus J. Bacchi

  DOI：10.1016/s0968-0896(97)00157-0

  日期：1997.12

  Trypanothione reductase (TR) occurs exclusively in trypanosomes and leishmania, which are the etiological agents of many diseases. TR plays a vital role in the antioxidant defenses of these parasites and inhibitors of TR have potential as antitrypanosomal agents. We describe the syntheses of several spermine and spermidine derivatives and the inhibiting effects of these compounds on T. cruzi TR. All of the inhibiting compounds displayed competitive inhibition of TR-mediated reduction of trypanothione disulfide. The three most effective compounds studied were N-4,N-8-bis(3-phenylpropyl)spermine (12), N-4,N-8-bis(2-naphthylmethyl)spermine (14), and N-1,N-8-bis(2-naphthylmethyl)spermidine (21), with K-i values of 3.5, 5.5 and 9.5 mu M, respectively. Compounds 12, 14, and 21 were found to be potent trypanocides in vitro with IC50 values ranging from 0.19 to 0.83 mu M against four T. brucei ssp. strains. However, these compounds did not prolong the lives of mice infected with trypanosomes. This work indicates that certain polyamine derivatives which target a unique pathway in Trypanosomatidae have potential as antitrypanosomal agents. (C) 1997 Elsevier Science Ltd.
• Antimalarial polyamine analogs
  作者：Michael L. Edwards、D. M. Stemerick、A. J. Bitonti、J. A. Dumont、P. P. McCann、P. Bey、A. Sjoerdsma

  DOI：10.1021/jm00106a015

  日期：1991.2

  A series of novel tetraamines of the general formula RNH(CH2)(x)NH(CH2)(y)(NH(CH2)(x)NHR was synthesized and examined for activity against growth of Plasmodium falciparum in vitro. Within the series, dibenzyl analogues (R = benzyl) were found to be the most effective growth inhibitors, with IC50 values of about 10-6 M. Further modifications of the tetraamine provided the optimum chain length for antimalarial activity of y = 7, x = 3. Compound 8 (MDL 27,695) with the structure y = 7, x = 3, R = benzyl, in combination with the ornithine decarboxylase inhibitor alpha-(difluoromethyl)ornithine, resulted in radical cures when tested against experimental Plasmodium berghei infections in mice. The structure-activity relationships of the series are discussed.
• US6114394A
  申请人：——

  公开号：US6114394A

  公开（公告）日：2000-09-05
• SUR QUELQUES DÉRIVÉS PHOSPHORES DE LA SPERMINE
  作者：Thëodorine Bailly、Ramon Burgada

  DOI：10.1080/10426509608037952

  日期：1996.8.1

  Abstract The reaction of spermine with aromatic aldehyde leads to an equilibrated system between the bis imine form 1' and the hexahydropyrimidine form 1. In contrary the formaldehyde adduct of spermine exist only on the hexahydropyrimidine form 9. 1–1' is readily hydrolyzed by HCl with regeneration of the aldehyde and spermine. The NaBH4, reduction of 1–1' leads to the dibenzyl spermine 8 and the

  摘要 精胺与芳香醛的反应导致双亚胺 1' 型和六氢嘧啶 1 型之间的平衡体系。相反，精胺的甲醛加合物仅存在于六氢嘧啶 9 型上。1-1' 很容易被 HCl 水解随着醛和精胺的再生。NaBH4，1-1' 的还原导致二苄基精胺 8 和膦酸加合物 2 或 6 从 1-1' 和膦酸氢盐获得。最后两个反应以 9 失败。相反，9 和 1-1' 与四甲基氯二氧杂磷杂环戊烷反应良好，形成环亚膦酰胺 10 和 5。在第二种情况下，可以通过 31P NMR 观察到动力学中间体 3。