N⁴,N⁹-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile | 194808-59-8

• 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: N⁴,N⁹-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile
• 英文别名: N(4),N(9)-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propionitrile；Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamate)；tert-butyl N-(2-cyanoethyl)-N-[4-[2-cyanoethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butyl]carbamate
• CAS: 194808-59-8
• 化学式: C₂₀H₃₄N₄O₄
• 分子量: 394.514
• InChiKey: AJGMQGBTCUVDON-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  544.3±50.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N⁴,N⁹-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile 在 镍 sodium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 194.0h， 生成 (2R)-2-amino-N-[3-[4-[3-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]propylamino]butylamino]propyl]-3-sulfanylpropanamide
  参考文献：
  名称：

  Template Oligomerization of DNA-Bound Cations Produces Calibrated Nanometric Particles

  摘要：

  DOI：

  10.1021/ja980620o
• 作为产物：
  描述：

  N,N’-二氰基乙基-1,4-丁烷二胺 、 2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 在 三乙胺 作用下， 反应 72.0h， 生成 N⁴,N⁹-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile
  参考文献：
  名称：

  Template Oligomerization of DNA-Bound Cations Produces Calibrated Nanometric Particles

  摘要：

  DOI：

  10.1021/ja980620o

文献信息

• Discovery of Novel Alkylated (bis)Urea and (bis)Thiourea Polyamine Analogues with Potent Antimalarial Activities
  作者：Bianca K. Verlinden、Jandeli Niemand、Janette Snyman、Shiv K. Sharma、Ross J. Beattie、Patrick M. Woster、Lyn-Marie Birkholtz

  DOI：10.1021/jm200463z

  日期：2011.10.13

  A series of alkylated (bis)urea and (bis)thiourea polyamine analogues were synthesized and screened for antimalarial activity against chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. All analogues showed growth inhibitory activity against P. falciparum at less than 3 μM, with the majority having effective IC50 values in the 100–650 nM range. Analogues arrested parasitic

  合成了一系列烷基化（双）脲和（双）硫脲多胺类似物，并在体外筛选了对氯喹敏感和耐药株恶性疟原虫的抗疟活性。所有类似物在小于 3 μM 时均显示出对恶性疟原虫的生长抑制活性，其中大多数具有100–650 nM 范围内的有效 IC 50值。由于核分裂和无性发育的阻滞，类似物在暴露后 24 小时内阻止了寄生生长。此外，这种作用似乎对疟原虫具有细胞毒性和高度选择性（对恶性疟原虫的IC 50低 7000 倍以上）) 并且通过多胺的外源加成是不可逆的。随着含有 3-7-3 或 3-6-3 个碳骨架和取代的末端脲或硫脲部分的多胺类似物的强效抗疟活性的首次报道，我们提出这些化合物代表了一类结构新颖的抗疟药。
• Polyamine functionalized carbon nanotubes: synthesis, characterization, cytotoxicity and siRNA binding
  作者：Prabhpreet Singh、Cristian Samorì、Francesca Maria Toma、Cyrill Bussy、Antonio Nunes、Khuloud T. Al-Jamal、Cécilia Ménard-Moyon、Maurizio Prato、Kostas Kostarelos、Alberto Bianco

  DOI：10.1039/c0jm04064a

  日期：——

  In this work we have synthesized a new series of cationic carbon nanotubes (CNTs) for siRNA binding. Both single- and multi-walled CNTs have been modified by addition or amidation reaction with short linear polyamine chains including putrescine, spermidine and spermine. All the new conjugates have been characterized with several spectroscopic and microscopic techniques. Their cytotoxic effects have been assessed on human lung carcinoma cell line. Finally, we have analyzed their capacity to bind siRNA towards the development of new carriers for gene silencing applications. The dispersibility properties and the capacity to complex siRNA of the different conjugates were found to be strongly dependent on the position of the functional groups on CNTs (i.e. mainly at the tips following the amidation reaction or on the sidewalls by direct C–C addition).

  在这项工作中，我们合成了一系列新型阳离子碳纳米管（CNTs）用于小干扰RNA（siRNA）的结合。通过添加或酰胺化反应，单壁和多壁碳纳米管均被改性，引入了包括腐胺、精胺和亚精胺在内的短链聚胺。所有新型共轭物均通过多种光谱和显微技术进行了表征。它们的细胞毒性在人肺癌癌细胞系上进行了评估。最后，我们分析了它们结合siRNA的能力，旨在开发用于基因沉默应用的新型载体。不同共轭物的分散性特性和结合siRNA的能力被发现强烈依赖于功能基团在碳纳米管上的位置（即主要在末端，通过酰胺化反应引入；或在侧壁上，通过直接C–C添加反应引入）。
• Solid-Phase synthesis of diamine and polyamine amino acid derivatives as HIV-1 tat-TAR binding inhibitors
  作者：G Jimenez Bueno、T Klimkait、I.H Gilbert、C Simons

  DOI：10.1016/s0968-0896(02)00305-x

  日期：2003.1

  A series of diamine and polyamine derivatives, either free amines or salts (HCl or TFA), of aspartic and glutamic acid were prepared in excellent yields using Rink Amide solid-phase synthesis. The asparagine and glutamine derivatives were all evaluated for their ability to inhibit Tat-TAR binding using a FIGS cellular assay, with the polyamine derivatives exhibiting the most promising binding activity

  使用Rink Amide固相合成，可以极好的收率制备一系列天冬氨酸和谷氨酸的二胺和多胺衍生物，无论是游离胺还是盐（HCl或TFA）。使用FIGS细胞测定法评估了所有天冬酰胺和谷氨酰胺衍生物抑制Tat-TAR结合的能力，其中多胺衍生物表现出最有希望的结合活性。
• Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation
  作者：Faiz Ahmed Khan、Saeed Ahmad、Naveena Kodipelli、Gururaj Shivange、Roy Anindya

  DOI：10.1039/c3ob42537a

  日期：——

  A–C are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A–C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library

  Ianthelliformisamines A–C是一类新的从溴酪氨酸衍生的抗菌剂，最近从海洋海绵Suberea ianthelliformis中分离出来。我们通过（E的缩合直接合成了邻苯二甲胺）-3-（3,5-二溴-4-甲氧基苯基）丙烯酸和相应的Boc保护的多胺，然后用TFA进行Boc脱保护。此外，使用该反应方案，通过使用3-苯基丙烯酸衍生物和Boc保护的多胺链，通过这两个片段的不同组合（苯环取代，双键几何结构或链不同），合成了其类似物（39个类似物）的文库多胺链中央间隔基团的长度（以红色显示）。筛选所有合成的化合物（苯乙酰胺胺A–C及其类似物）对革兰氏阴性菌（大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌）的抗菌活性）株。苯乙酰胺胺A的所有合成类似物均对两种菌株（大肠杆菌和金黄色葡萄球菌）均显示出细菌生长抑制作用，MIC值在117.8–0.10μM范围内，而苯乙酰胺胺C的任何合成类似物以及母
• Synthesis and Biological Evaluation of <i>s</i>-Triazine Substituted Polyamines as Potential New Anti-Trypanosomal Drugs
  作者：Burkhard Klenke、Mhairi Stewart、Michael P. Barrett、Reto Brun、Ian H. Gilbert

  DOI：10.1021/jm010854+

  日期：2001.10.1

  The P2 transporter is a nucleoside transporter which is unique to the protozoan parasite Trypanosoma brucei, the causative organism of Human African Trypanosomasis. The transporter has been shown to bind some structural motifs not recognized by other transporters. In this paper we describe the use of the melamine motif, a substrate of the P2 transporter, as a potential tool to selectively deliver polyamine analogues to the parasites. The synthesis of a number of polyamine analogues attached to a variety of melamine analogues is described. Many of the compounds were shown to competitively inhibit uptake of adenosine, indicating that they are recognized by the transporter. Some of the compounds showed good in vitro activity against the parasites.