Carbamic acid, 1,4-butanediylbis[[3-[(trifluoroacetyl)amino]propyl]-, phenylmethyl phenylmethyl ester | 202145-89-9

• 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: Carbamic acid, 1,4-butanediylbis[[3-[(trifluoroacetyl)amino]propyl]-, phenylmethyl phenylmethyl ester
• 英文别名: benzyl N-[4-[phenylmethoxycarbonyl-[3-[(2,2,2-trifluoroacetyl)amino]propyl]amino]butyl]-N-[3-[(2,2,2-trifluoroacetyl)amino]propyl]carbamate
• CAS: 202145-89-9
• 化学式: C₃₀H₃₆F₆N₄O₆
• 分子量: 662.629
• InChiKey: FMRNDEFTGOCQIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Carbamic acid, 1,4-butanediylbis[[3-[(trifluoroacetyl)amino]propyl]-, phenylmethyl phenylmethyl ester 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以91%的产率得到benzyl N-(3-aminopropyl)-N-[4-[3-aminopropyl(benzyloxycarbonyl)amino]butyl]carbamate
  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
• 作为产物：
  描述：

  氯甲酸苄酯 、 N¹,N¹⁴-bis(trifluoroacetyl)spermine ditrifluoroacetate 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到Carbamic acid, 1,4-butanediylbis[[3-[(trifluoroacetyl)amino]propyl]-, phenylmethyl phenylmethyl ester
  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