N-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine | 158474-89-6

• 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: N-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine
• 英文别名: N¹,N⁸-bis(trifluoroacetyl)spermidine；2,2,2-trifluoro-N-[4-[3-[(2,2,2-trifluoroacetyl)amino]propylamino]butyl]acetamide
• CAS: 158474-89-6
• 化学式: C₁₁H₁₇F₆N₃O₂
• 分子量: 337.265
• InChiKey: PJFHRRVCKBIDSR-UHFFFAOYSA-N

物化性质

• 沸点：
  411.5±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine 在 ammonium hydroxide 、 potassium carbonate 、 caesium carbonate 、 苯硫酚 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 51.0h， 生成 3,12-Bis-(3-bromo-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene
  参考文献：
  名称：

  Solution Phase Combinatorial Chemistry. Discovery of Novel Polyazapyridinophanes with Potent Antibacterial Activity by a Solution Phase Simultaneous Addition of Functionalities Approach

  摘要：

  Chemical modification of pre-formed asymmetric polyazaphane scaffolds by simultaneous addition of Functionality (letters) in solution has been developed for the preparation of tertiary nitrogen-based combinatorial chemistry libraries. This approach has some significant advantages over the more commonly employed solid phase bead splitting/resction/mixing procedures for the preparation of libraries. Three novel, asymmetric polyazaphanes 32, 33, and 37 have been synthesized in high yields by an efficient cyclization of 2,6-bis(bronzomethyl)pyridine (31) with new orthogonally protected triamines 29, 30, and 35, respectively. Selective deprotection of 32, 33, and 37 provided mono-t-Boc-protected scaffolds 1-3 suitable for solution phase, simultaneous addition of functionalities. Model studies of small libraries of scaffold 2 using CZE analyses indicated that simultaneous addition of 10 benzylic bromide alkylating functionalities would result in libraries containing approximately equimolar amounts of all possible compounds. Sixteen purified tertiary amine libraries 4-19 (total complexity of 1600 compounds) were generated by this procedure from scaffold 2. A ''fix-last'' combinatorial method was devised to minimize chemical reactions. Several first-round sublibraries of scaffold 2, containing a mixture of 100 compounds, exhibited potent antimicrobial activities. Twenty single compounds 63-82 with uniform functionalities at the combinatorialized sites were synthesized. Some of these pure compounds were more active, while others were less active, compared with the parent mixtures 5 and 10.

  DOI：

  10.1021/ja964153r
• 作为产物：
  描述：

  亚精胺 、 三氟乙酸乙酯 在 水 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以89%的产率得到N-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine
  参考文献：
  名称：

  Discrimination of spermidine amino functions by a new protecting group strategy; application to the synthesis of guanidinylated polyamines, including hirudonine

  摘要：

  从尸胺和亚精胺分别合成的阿基美汀和水蛭素是通过采用一种新的聚胺保护基团策略实现的，该策略使用N-硝基氨基脲作为氨基功能的前体，并选择性地在N-1和N-8位用三氟乙酰基保护亚精胺，而在N-4位用4-叠氮苯甲氧羰基进行保护。

  DOI：

  10.1039/c39940002613

文献信息

• New spermine and spermidine derivatives as potent inhibitors of Trypanosoma cruzi Trypanothione Reductase
  作者：Béatrice Bonnet、David Soullez、Elisabeth Davioud-Charvet、Valérie Landry、Dragos Horvath、Christian Sergheraert

  DOI：10.1016/s0968-0896(97)00070-9

  日期：1997.7

  Several spermine and spermidine derivatives containing 2-amino diphenylsulfide substituents were prepared and tested for their inhibiting effects on Trypanosoma cruzi trypanothione reductase. IC50 values were assessed between 0.3 and 3 microM. Compound 32 (Ki = 0.4 microM) is the most potent TR inhibitor described so far.

  制备了几种含有2-氨基二苯硫醚取代基的精胺和亚精胺衍生物，并测试了它们对克氏锥虫锥虫硫醇还原酶的抑制作用。IC50值评估为0.3至3 microM。化合物32（Ki = 0.4 microM）是迄今为止描述的最有效的TR抑制剂。
• Solid phase polyamine linkers-their utility in synthesis and the preparation of directed libraries against trypanothione reductase
  作者：Ian R. Marsh、Helen Smith、Mark Bradley

  DOI：10.1039/cc9960000941

  日期：——

  A variety of diprotected polymines are anchored to a solid support and used in solid phase chemistry and library generation.

  各种二保护多胺被锚定在固体支持物上，并用于固相化学和生成库。
• Combination of Antimicrobial and Endotoxin-Neutralizing Activities of Novel Oleoylamines
  作者：Mateja Zorko、Andreja Majerle、David Šarlah、Mateja Manček Keber、Barbara Mohar、Roman Jerala

  DOI：10.1128/aac.49.6.2307-2313.2005

  日期：2005.6

  A combination of antimicrobial and endotoxin-neutralizing activities is desired in order to prevent progression from infection to sepsis due to the release of lipopolysaccharide from dying gram-negative bacteria. Lipopolyamines have emerged as a new type of endotoxin-neutralizing compound, but their antimicrobial activity has not been investigated. We synthesized a series of 10 oleoylamines differing in the polyamino head group, particularly in the number and separation between nitrogen atoms and the position of the oleoyl moiety. Compounds showed activity against both gram-negative and gram-positive bacteria in the micromolar range. Compounds were able to provide penetration of ethidium bromide into bacteria, indicating effects on the bacterial membrane. Oleoylamines neutralized endotoxin inLimulusamoebocyte lysate assays and by neutralization of tumor necrosis factor alpha release in human blood. Comparison of biological activities of compounds identified structural properties responsible for antimicrobial activity, and quantitative structure-property relationship analysis provided a quantitative model for prediction of activity of oleoylamines.

  摘要：为了防止由于濒死的革兰氏阴性细菌释放脂多糖而导致感染发展为败血症，我们需要将抗菌活性和中和内毒素活性结合起来。脂多胺是一种新型的内毒素中和化合物，但其抗菌活性尚未得到研究。我们合成了一系列 10 种油酰基胺，它们在多氨基头基，特别是氮原子的数量和间隔以及油酰基的位置上各不相同。这些化合物在微摩尔范围内对革兰氏阴性菌和革兰氏阳性菌都具有活性。化合物能够使溴化乙锭渗透到细菌中，这表明它们对细菌膜产生了作用。油酰基胺能中和利木赞阿米巴细胞裂解物试验中的内毒素，并能中和人体血液中肿瘤坏死因子α的释放。对化合物的生物活性进行比较，确定了导致抗菌活性的结构特性，定量结构-特性关系分析为预测油酰基胺的活性提供了一个定量模型。
• 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。
• AMIDE AND PEPTIDE DERIVATIVES OF DIALKYLENETRIAMINES AND THEIR USE AS TRANSFECTION AGENTS
  申请人：Castro Mariano Javier

  公开号：US20090209472A1

  公开（公告）日：2009-08-20

  This invention relates to newly identified spermidine based surfactant compounds, to the use of such compounds and to their production. The invention also relates to the use of the spermidine based compounds to facilitate the transfer of polynucleotides into cells.

  本发明涉及新鉴定的以精胺为基础的表面活性剂化合物，以及这些化合物的使用和生产。该发明还涉及使用以精胺为基础的化合物促进多核苷酸进入细胞的方法。