N,N'-Bis-(3-amino-propyl)-N,N'-bis-(3-phenyl-propyl)-butane-1,4-diamine | 168101-41-5

• 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-amino-propyl)-N,N'-bis-(3-phenyl-propyl)-butane-1,4-diamine
• 英文别名: N,N'-bis(3-aminopropyl)-N,N'-bis(3-phenylpropyl)butane-1,4-diamine
• CAS: 168101-41-5
• 化学式: C₂₈H₄₆N₄
• 分子量: 438.7
• InChiKey: YUQMYWBOSYVNIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-Bis-(3-amino-propyl)-N,N'-bis-(3-phenyl-propyl)-butane-1,4-diamine 在 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-{3-[{4-[(3-Amino-propyl)-(3-phenyl-propyl)-amino]-butyl}-(3-phenyl-propyl)-amino]-propyl}-guanidine
  参考文献：
  名称：

  Polyamines and the NMDA receptor: Modifying intrinsic activities with aromatic substituents

  摘要：

  Thirty-four spermidine (SPD) and spermine (SPM) derivatives with aromatic substituents were synthesized and tested as inhibitors of specific binding of the NMDA channel blocker [H-3]MK-801 to membranes prepared from rat hippocampus and cerebral cortex. SPD and SPM derivatives with aromatic substituents at the primary amino groups were the most potent inhibitors (IC50 3.9-4.7 mu M). These compounds most likely act directly at the NMDA ion channel, since 30 pM SPM had no pronounced influence on their inhibiting activities. SPD derivatives with aromatic substituents at the secondary amino group were either inactive or highly SPM-sensitive inhibitors (IC50 10-82 mu M), depending on the size of the substituent. Our results support the hypothesis that an aromatic interaction site near the center of polyamine derivatives contributes to polyamine inverse agonism. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.015
• 作为产物：
  描述：

  N⁴,N⁸-bis(3-phenylpropyl)-N¹,N¹²-bis(trifluoroacetyl)spermine 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以79%的产率得到N,N'-Bis-(3-amino-propyl)-N,N'-bis-(3-phenyl-propyl)-butane-1,4-diamine
  参考文献：
  名称：

  Polyamine derivatives as inhibitors of trypanothione reductase and assessment of their trypanocidal activities

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(97)00157-0

文献信息

• Polyamines with N -(3-phenylpropyl) substituents are effective competitive inhibitors of trypanothione reductase and trypanocidal agents
  作者：Zhili Li、Michael W Fennie、Bruce Ganem、Matthew T Hancock、Muris Kobašlija、Donna Rattendi、Cyrus J Bacchi、Mary C O'Sullivan

  DOI：10.1016/s0960-894x(00)00643-0

  日期：2001.1

  Several N-(3-phenylpropyl)-substituted spermidine and spermine derivatives were prepared and found to be potent competitive inhibitors of Trypanosoma cruzi trypanothione reductase (seven compounds with K-i values < 5 M are described). The most effective inhibitor studied was compound 12 with a K-i value of 0.151 muM. Six of the compounds described are also effective trypanocides with IC50 values <1 M. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.
• Polyamines and the NMDA receptor: Modifying intrinsic activities with aromatic substituents
  作者：Michael L. Berger、Abdallah Y. Bitar、Matthew J. Waitner、Patrick Rebernik、Mary C. O’Sullivan

  DOI：10.1016/j.bmcl.2006.03.015

  日期：2006.6

  Thirty-four spermidine (SPD) and spermine (SPM) derivatives with aromatic substituents were synthesized and tested as inhibitors of specific binding of the NMDA channel blocker [H-3]MK-801 to membranes prepared from rat hippocampus and cerebral cortex. SPD and SPM derivatives with aromatic substituents at the primary amino groups were the most potent inhibitors (IC50 3.9-4.7 mu M). These compounds most likely act directly at the NMDA ion channel, since 30 pM SPM had no pronounced influence on their inhibiting activities. SPD derivatives with aromatic substituents at the secondary amino group were either inactive or highly SPM-sensitive inhibitors (IC50 10-82 mu M), depending on the size of the substituent. Our results support the hypothesis that an aromatic interaction site near the center of polyamine derivatives contributes to polyamine inverse agonism. (c) 2006 Elsevier Ltd. All rights reserved.