N¹-(2-{bis[2-(3-amino-propylamino)ethyl]-amino}-ethyl)-propane-1,3-diamine | 239810-49-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹-(2-{bis[2-(3-amino-propylamino)ethyl]-amino}-ethyl)-propane-1,3-diamine
• 英文别名: N'-[2-[bis[2-(3-aminopropylamino)ethyl]amino]ethyl]propane-1,3-diamine
• CAS: 239810-49-2
• 化学式: C₁₅H₃₉N₇
• 分子量: 317.522
• InChiKey: LACRWQGZEANYTF-UHFFFAOYSA-N

物化性质

• 沸点：
  477.2±40.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  117
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N¹-(2-{bis[2-(3-amino-propylamino)ethyl]-amino}-ethyl)-propane-1,3-diamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N-9-anthrylmethyl-N'-(2-bis{2-[3-aminopropylamino]ethyl}aminoethyl)-1,3-propanediamine
  参考文献：
  名称：

  Cu²⁺and AMP complexation of enlarged tripodal polyamines

  摘要：

  报告介绍了三种三足多胺的合成、特性、Cu2+ 配位以及与 AMP 的相互作用。这些多胺以四胺（tren）的结构为基础，而四胺的三个丙基氨基官能团（TAL）、一个末端主硝基上的另一个蒽甲基片段（ATAL）或三个末端的萘甲基片段（N3TAL）被放大。所有这三种多胺的质子化常数都表明，在 pH 值为 6 时，多胺臂上的所有六个一级和二级氮原子都质子化。通过电位测定法、紫外-可见光谱法、ESI-MS 光谱法和核磁共振技术研究了 TAL 和 ATAL 与 Cu2+ 和 AMP（腺苷-5′-单磷酸）的相互作用。pH-计量、核磁共振和 ESI/MS 技术表明，TAL 和 ATAL 与 AMP 在水中形成的 AMP : L 加合物的化学计量比分别为 1 : 1、2 : 1 和 3 : 1。这是首次在水溶液中形成此类复合物的实例之一。观察到 TAL、ATAL、N3TAL、Cu2+ 和 AMP 之间形成了三元复合物。我们利用顺磁核磁共振技术获得了 AMP 与 Cu2+-TAL 双核络合物结合模式的结构信息。

  DOI：

  10.1039/b605639c
• 作为产物：
  描述：

  tris[2-(N-tosylaminoethyl)]amine 在 氢溴酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 N¹-(2-{bis[2-(3-amino-propylamino)ethyl]-amino}-ethyl)-propane-1,3-diamine
  参考文献：
  名称：

  Intramolecular Excimer Formation in a Tripodal Polyamine Receptor Containing Three Naphthalene Fluorophores

  摘要：

  comprehensive investigation on the energetics and dynamics of a new fluorescent sensor constituted by a tripodal polyamine receptor containing three naphthalene fluorophores, compound L, is reported. The influence of external factors such as the solvent, hydrogen ion concentration, and temperature in the photophysics of the sensor is discussed. The temperature dependence of monomer/excimer interconversion of L revealed an average percentage relative sensitivity of 4.5%/degreesC thus portending its use as a temperature sensor. The activation energy for excimer formation (E-1 = 12 kJ mol(-1)) and dissociation (E-1 = 57 kJ mol(-1)), entropy change (DeltaS = -128 J K-1 mol(-1)), and the binding energy of the excimer (DeltaH = 45 kJ mol(-1)) were obtained in water at acidic pH values and ethanol (E-1 = 15 kJ mol(-1), E-1 = 40 kJ mol(-1), DeltaS = -61 J K-1 mol(-1), and DeltaH = 25 kJ mol(-1)). The dependence of the kinetic and thermodynamic parameters on the dielectric constant of the medium and on the degree of protonation of the polyamine chain was interpreted in terms of the excimer destabilization provoked by the electrostatic repulsion between the positively charged chains.

  DOI：

  10.1021/jp0343032

文献信息

• Acid–base properties of functionalised tripodal polyamines and their interaction with nucleotides and nucleic acids
  作者：Alejandra Sornosa-Ten、M. Teresa Albelda、Juan C. Frías、Enrique García-España、José M. Llinares、Ana Budimir、Ivo Piantanida

  DOI：10.1039/c000124d

  日期：——

  Novel, highly positively charged tripodal polyamines with appended heterocyclic moieties revealed an intriguing panel of protonation species within the biologically relevant range. Studied compounds bind nucleotide monophosphates by mostly electrostatic interactions but only the imidazole analogue showed selectivity toward UMP in respect to other nucleotides. Strong binding of all the studied compounds to both ds-DNA and ds-RNA is to some extent selective toward the latter, showing rather rare RNA over DNA preference.

  具有附加杂环基团的新型高正电荷三聚多胺在生物相关范围内显示出一系列有趣的质子化物种。所研究的化合物主要通过静电相互作用与单磷酸核苷酸结合，但只有咪唑类似物对UMP表现出选择性，而其他核苷酸则没有。所有研究化合物与双链DNA和双链RNA的结合强度在一定程度上对后者具有选择性，表现出罕见的RNA优先于DNA的现象。
• Antimicrobial Properties of New Polyamines Conjugated with Oxygen-Containing Aromatic Functional Groups
  作者：Mario Inclán、Neus Torres Hernández、Alejandro Martínez Serra、Gonzalo Torrijos Jabón、Salvador Blasco、Cecilia Andreu、Marcel lí del Olmo、Beatriz Jávega、José-Enrique O’Connor、Enrique García-España

  DOI：10.3390/molecules28227678

  日期：——

  (linear, tripodal, and macrocyclic) and their derivatives with the oxygen-containing aromatic functional groups 1,3-benzodioxol, ortho/para phenol, or 2,3-dihydrobenzofuran. The new compounds were prepared through an inexpensive process, and their activity was tested against selected strains of yeast, as well as Gram-positive and Gram-negative bacteria. In all cases, the conjugated derivatives showed antimicrobial

  抗生素耐药性现在是一个首要的健康问题，这使得开发新的抗菌药物家族势在必行。理想情况下，这些化合物应该是廉价的、容易获得的、高活性的和无毒的。在此，我们介绍了一系列具有不同结构（线性、三足和大环）的天然和合成多胺及其具有含氧芳香族官能团 1,3-苯并间二氧杂环己烷、邻位二氧杂环己烷的衍生物的抗菌活性的研究结果。对苯酚，或2,3-二氢苯并呋喃。这些新化合物是通过廉价的工艺制备的，并针对选定的酵母菌株以及革兰氏阳性和革兰氏阴性细菌测试了它们的活性。在所有情况下，共轭衍生物表现出比未取代的多胺更高的抗菌活性。生理 pH 值下的总电荷、亲脂性和多胺支架的拓扑结构等几个因素与其活性相关。亲脂部分的性质也是人类细胞毒性的决定因素。研究发现，这些先导化合物具有杀菌和抑菌作用，并且与商业抗真菌药物氟康唑、放线菌酮和两性霉素 B 对所测试的酵母菌株具有协同作用。
• Linear, tripodal, macrocyclic: Ligand geometry and ORR activity of supported Pd(II) complexes
  作者：Matteo Savastano、Maurizio Passaponti、Walter Giurlani、Leonardo Lari、Nicola Calisi、Estefanía Delgado-Pinar、Elena Salvador Serrano、Enrique Garcia-España、Massimo Innocenti、Vlado K. Lazarov、Antonio Bianchi

  DOI：10.1016/j.ica.2021.120250

  日期：2021.4
• Cu²⁺and AMP complexation of enlarged tripodal polyamines
  作者：M. Teresa Albelda、Enrique García-España、Hermas R. Jiménez、José M. Llinares、Conxa Soriano、Alejandra Sornosa-Ten、Begoña Verdejo

  DOI：10.1039/b605639c

  日期：——

  The synthesis, characterization, Cu2+ coordination and interaction with AMP of three tripodal polyamines are reported. The polyamines are based on the structure of the tetraamine (tren) which has been enlarged with three propylamino functionalities (TAL), with a further anthrylmethyl fragment at one of its terminal primary nitrogens (ATAL) or with naphthylmethyl fragments at its three ends (N3TAL). The protonation constants of all three polyamines show that at pH 6, all six primary and secondary nitrogen atoms in the arms are protonated. The interaction with Cu2+ and AMP (adenosine-5′-monophosphate) has been studied by potentiometric, UV-Vis, ESI-MS spectroscopy and NMR techniques. pH-Metric, NMR and ESI/MS techniques indicate that TAL and ATAL form with AMP adducts of 1 : 1, 2 : 1 and 3 : 1 AMP : L stoichiometries in water. This is one of the first examples for the formation of such complexes in aqueous solution. Formation of ternary complexes between TAL, ATAL, N3TAL, Cu2+ and AMP is observed. Paramagnetic NMR techniques have been used to obtain structural information on the binding mode of AMP to the Cu2+–TAL binuclear complexes.

  报告介绍了三种三足多胺的合成、特性、Cu2+ 配位以及与 AMP 的相互作用。这些多胺以四胺（tren）的结构为基础，而四胺的三个丙基氨基官能团（TAL）、一个末端主硝基上的另一个蒽甲基片段（ATAL）或三个末端的萘甲基片段（N3TAL）被放大。所有这三种多胺的质子化常数都表明，在 pH 值为 6 时，多胺臂上的所有六个一级和二级氮原子都质子化。通过电位测定法、紫外-可见光谱法、ESI-MS 光谱法和核磁共振技术研究了 TAL 和 ATAL 与 Cu2+ 和 AMP（腺苷-5′-单磷酸）的相互作用。pH-计量、核磁共振和 ESI/MS 技术表明，TAL 和 ATAL 与 AMP 在水中形成的 AMP : L 加合物的化学计量比分别为 1 : 1、2 : 1 和 3 : 1。这是首次在水溶液中形成此类复合物的实例之一。观察到 TAL、ATAL、N3TAL、Cu2+ 和 AMP 之间形成了三元复合物。我们利用顺磁核磁共振技术获得了 AMP 与 Cu2+-TAL 双核络合物结合模式的结构信息。
• Intramolecular Excimer Formation in a Tripodal Polyamine Receptor Containing Three Naphthalene Fluorophores
  作者：M. Teresa Albelda、Enrique García-España、Laura Gil、João C. Lima、Carlos Lodeiro、J. Seixas de Melo、M. João Melo、A. Jorge Parola、Fernando Pina、Conxa Soriano

  DOI：10.1021/jp0343032

  日期：2003.7.1

  comprehensive investigation on the energetics and dynamics of a new fluorescent sensor constituted by a tripodal polyamine receptor containing three naphthalene fluorophores, compound L, is reported. The influence of external factors such as the solvent, hydrogen ion concentration, and temperature in the photophysics of the sensor is discussed. The temperature dependence of monomer/excimer interconversion of L revealed an average percentage relative sensitivity of 4.5%/degreesC thus portending its use as a temperature sensor. The activation energy for excimer formation (E-1 = 12 kJ mol(-1)) and dissociation (E-1 = 57 kJ mol(-1)), entropy change (DeltaS = -128 J K-1 mol(-1)), and the binding energy of the excimer (DeltaH = 45 kJ mol(-1)) were obtained in water at acidic pH values and ethanol (E-1 = 15 kJ mol(-1), E-1 = 40 kJ mol(-1), DeltaS = -61 J K-1 mol(-1), and DeltaH = 25 kJ mol(-1)). The dependence of the kinetic and thermodynamic parameters on the dielectric constant of the medium and on the degree of protonation of the polyamine chain was interpreted in terms of the excimer destabilization provoked by the electrostatic repulsion between the positively charged chains.