N¹,N¹⁴-bis(trifluoroacetyl)spermine ditrifluoroacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N¹,N¹⁴-bis(trifluoroacetyl)spermine ditrifluoroacetate
• 英文别名: N1,N14-bis(trifluoroacetyl)spermine di(trifluoroacetic acid) salt；N1,N12-bis(trifluoroacetyl)spermine bis(trifluoroacetate)；2,2,2-trifluoroacetic acid;2,2,2-trifluoro-N-[3-[4-[3-[(2,2,2-trifluoroacetyl)amino]propylamino]butylamino]propyl]acetamide
• 化学式: 2C₂HF₃O₂*C₁₄H₂₄F₆N₄O₂
• 分子量: 622.408
• InChiKey: ACEVALSGCBCVGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N¹,N¹⁴-bis(trifluoroacetyl)spermine ditrifluoroacetate 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 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：

  精胺 、 三氟乙酸乙酯 在 水 作用下， 以 乙腈 为溶剂， 以93%的产率得到N¹,N¹⁴-bis(trifluoroacetyl)spermine ditrifluoroacetate
  参考文献：
  名称：

  多胺伯氨基选择性三氟乙酰化的一步法

  摘要：

  多胺与三氟乙酸乙酯在湿乙腈中的反应导致伯氨基的选择性三氟乙酰化。已表明该反应适用于多种多胺。

  DOI：

  10.1016/0040-4039(95)00630-u

文献信息

• A one-step procedure for the selective trifluoroacetylation of primary amino groups of polyamines
  作者：Mary C. O'Sullivan、Damon M. Dalrymple

  DOI：10.1016/0040-4039(95)00630-u

  日期：1995.5

  The reaction of polyamines with ethyl trifluoroacetate in wet acetonitrile results in the selective trifluoroacetylation of primary amino groups. This reaction is shown to be applicable to a range of polyamines.

  多胺与三氟乙酸乙酯在湿乙腈中的反应导致伯氨基的选择性三氟乙酰化。已表明该反应适用于多种多胺。
• Adjuvant
  申请人：Catchpole Ian Richard

  公开号：US20110045027A1

  公开（公告）日：2011-02-24

  The present invention provides a novel adjuvant for polynucleotide vaccines, and in particular the present invention provides immunogenic compositions comprising a polynucleotide encoding an antigen capable of eliciting an immune response and an adjuvant comprising an immunostimulatory quantity of a gemini surfactant, or a derivative thereof.

  本发明提供了一种新型的辅助剂，用于多核苷酸疫苗，特别是本发明提供了包含编码能够引起免疫反应的抗原的多核苷酸和包含免疫刺激量的双子星表面活性剂或其衍生物的辅助剂的免疫原性组合物。
• WO2006/136460
  申请人：——

  公开号：——

  公开（公告）日：——
• Polycationic Sulfonamides for the Sequestration of Endotoxin
  作者：Mark R. Burns、Scott A. Jenkins、Matthew R. Kimbrell、Rajalakshmi Balakrishna、Thuan B. Nguyen、Benjamin G. Abbo、Sunil A. David

  DOI：10.1021/jm061198m

  日期：2007.2.1

  Lipopolysaccharides (LPS) play a key role in the pathogenesis of septic shock, a major cause of mortality in the critically ill patient. We had previously shown that monoacylated polyamine compounds specifically bind to and neutralize the activity of LPS with high in vitro potency and afford complete protection in a murine model of endotoxic shock. Fatty acid amides of polyamines may be rapidly cleared from systemic circulation due to their susceptibility to nonspecific serum amidases and, thus, would be predicted to have a short duration of action. In a systematic effort to increase the likelihood of better bioavailability properties together with structural modifications that may result in gains in activity, we now report structure-activity relationships pertaining to endotoxin-binding and -neutralizing activities of homologated polyamine sulfonamides.
• Preparation of spermine conjugates with acidic retinoids with potent ribonuclease P inhibitory activity
  作者：George Magoulas、Dionysios Papaioannou、Evangelia Papadimou、Denis Drainas

  DOI：10.1016/j.ejmech.2009.01.001

  日期：2009.6

  Novel mono- and diacylated spermines, readily obtained using isolable succinimidyl active esters of acidic retinoids for the selective acylation of free spermine or in situ activated acidic retinoids for acylating selectively protected spermine followed by deprotection, were shown to inhibit the ribozyme ribonuclease P more strongly than the parent retinoids. (C) 2009 Elsevier Masson SAS. All rights reserved.