1,12-diphthalimido-4,9-diazadodecane | 104435-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,12-diphthalimido-4,9-diazadodecane
• 英文别名: 2-[3-[4-[3-(1,3-dioxoisoindol-2-yl)propylamino]butylamino]propyl]isoindole-1,3-dione
• CAS: 104435-59-8
• 化学式: C₂₆H₃₀N₄O₄
• 分子量: 462.549
• InChiKey: XVCLLIHDUKVDMU-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  640.7±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,12-diphthalimido-4,9-diazadodecane 在 六氯环三磷腈 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到
  参考文献：
  名称：

  Spermidine- and spermine-linked cyclophosphazenes: new forced (bi-dangling and spiro-bidangling) molecular configurations

  摘要：

  DOI：

  10.1016/0022-2860(88)80254-0
• 作为产物：
  描述：

  精胺 、 N-乙氧羰基邻苯二甲酰亚胺 以 氯仿 为溶剂， 反应 0.75h， 以61%的产率得到1,12-diphthalimido-4,9-diazadodecane
  参考文献：
  名称：

  In the Search for New Anticancer Drugs, XVI Selective Protection and Deprotection of Primary Amino Groups in Spermine, Spermidine and Other Polyamines

  摘要：

  摘要：Spermidine，spermine和其他多胺1-5在不影响次级氨基基团的情况下，通过使用N-乙氧羰基邻苯二甲酰亚胺（15），即Nefkens试剂，对末端主要氨基功能进行选择性保护。三种代表性产物17、18和20很容易在次级氨基氮上发生酰化，形成相应的化合物21-26。通过肼解两种代表性样品22和25的主要氨基功能的选择性去保护，得到具有游离主要氨基基团的相应衍生物27和28。 总之，Nefkens试剂在各种多胺中对末端主要氨基基团进行保护的应用，采用商业可获得试剂进行简单、高效和选择性的一步程序。

  DOI：

  10.1515/znb-1986-0125

文献信息

• Novel spermine-based cationic gemini surfactants for gene delivery
  作者：Gaël Ronsin、Christele Perrin、Philippe Guédat、Andreas Kremer、Patrick Camilleri、Anthony J. Kirby

  DOI：10.1039/b105936j

  日期：——

  Two types of spermine-based gemini surfactants have been synthesised; structure–activity studies have shown one type to be far superior in gene transection than the other.

  已经合成了两种基于精胺的双子表面活性剂；结构-活性研究表明，其中一种在基因横断方面远优于另一种。
• Compounds
  申请人：SmithKline Beecham p.l.c.

  公开号：US06835712B1

  公开（公告）日：2004-12-28

  Spermine:peptide-based surfactant compounds are disclosed. The compounds are based on a spermine backbone with peptide groups and optionally hydrocarbyl groups linked thereto. Uses of the spermine:peptide-based surfactant compounds and methods for their production are also disclosed.

  本发明公开了基于精胺骨架的肽类表面活性剂化合物。该化合物基于精胺骨架，具有肽基团和可选择地与之连接的烃基团。本发明还公开了使用该精胺：肽类表面活性剂化合物的方法以及它们的制备方法。
• Garrigues, Bernard; Vidaud, Lionel, Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 10, p. 775 - 786
  作者：Garrigues, Bernard、Vidaud, Lionel

  DOI：——

  日期：——
• Efficient Silencing of EGFP Reporter Gene with siRNA Delivered by Asymmetrical <i>N</i>⁴,<i>N</i>⁹-Diacyl Spermines
  作者：Abdelkader A. Metwally、Olivier Reelfs、Charareh Pourzand、Ian S. Blagbrough

  DOI：10.1021/mp200429n

  日期：2012.7.2

  It is important to obtain structure-activity relationship (SAR) data across cationic lipids for the self-assembly and nonviral intracellular delivery of siRNA. The aims of this work are to carry out a SAR study on the efficiency of asymmetrical N-4,N-9-diacyl spermines in siRNA delivery and EGFP reporter gene silencing, with comparisons to selected mixtures composed of symmetrical N-4,N-9-diacyl spermines. Another important aim of these studies is to quantify the changes in cell viability, assayed with alamarBlue, as a function of lipid structure. Therefore, we have designed, synthesized, purified, and assayed novel cationic lipids that are asymmetrical lipopolyamines based on spermine. Flow cytometry and fluorescence microscopy in an EGFP stably transfected HeLa cell line, measuring both delivery of fluorescently tagged siRNAs and silencing the EGFP signal, allowed quantitation of the differences between asymmetrical cationic lipids, mixtures of their symmetrical counterparts, and comparison with commercial nonviral delivery agents. Intracellular delivery of siRNA and gene silencing by siRNA differ with different hydrophobic domains. In these asymmetrical N-4,N-9-diacyl spermines, lipids that enhance siRNA uptake do not necessarily enhance siRNA-induced inhibition of gene expression: C18 and longer saturated chains promote uptake, while more unsaturated C18 chains promote gene silencing. These properties are efficiently demonstrated in a new nontoxic cationic lipid siRNA vector, N-4-linoleoyl-N-9-oleoyl-1,12-diamino-4,9-diazadodecane (LinOS), which is also shown to be comparable with or superior to TransIT-TKO and Lipofectamine 2000.
• Optimising inhibitors of Trypanothione reductase using solid-phase chemistry
  作者：Bordin Chitkul、Mark Bradley

  DOI：10.1016/s0960-894x(00)00471-6

  日期：2000.10

  A series of inhibitors of the enzyme trypanothione reductase has been identified using directed solid-phase chemistry. The compounds were based on a series of polyamine scaffolds and used the natural product kukoamine A as the lead structure. A compound with a K-i of 76 nM was identified, although somewhat surprisingly the compound appeared to be noncompetitive in nature. (C) 2000 Elsevier Science Ltd. All rights reserved.