N,N'-bis-{3-[4-(3-amino-propyl)piperazin-1-yl]propyl}-3,4,9,10-perylenebis(dicarboximide)

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis-{3-[4-(3-amino-propyl)piperazin-1-yl]propyl}-3,4,9,10-perylenebis(dicarboximide)
• 英文别名: 7,18-Bis[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone；7,18-bis[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• 化学式: C₄₄H₅₂N₈O₄
• 分子量: 756.948
• InChiKey: DRXZRZGREGCGJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  庚二酸 、 N,N'-bis-{3-[4-(3-amino-propyl)piperazin-1-yl]propyl}-3,4,9,10-perylenebis(dicarboximide) 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以5%的产率得到1,5,28,32,35,39,47,51-Octazadecacyclo[49.2.2.232,35.15,13.120,28.07,12.010,23.011,16.017,22.021,26]nonapentaconta-7,9,11(16),12,14,17(22),18,20,23,25-decaene-6,27,40,46,58,59-hexone
  参考文献：
  名称：

  Cyclic perylene diimide: Selective ligand for tetraplex DNA binding over double stranded DNA

  摘要：

  Synthesized cyclic perylene diimide, cPDI, showed the binding constant of 6.3 x 10(6) M-1 with binding number of n = 2 with TA-core as a tetraplex DNA in 50 mM Tris-HCl buffer (pH = 7.4) containing 100 mM KCl using Schatchard analysis and showed a higher preference for tetraplex DNA than for double stranded DNA with over 10(3) times. CD spectra showed that TA-core induced its antiparallel conformation upon addition of cPDI in the absence or presence of K+ or Na+ ions. The cPDI inhibits the telomerase activity with IC50 of 0.3 mu M using TRAP assay which is potential anti-cancer drug with low side effect. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.10.014
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到N,N'-bis-{3-[4-(3-amino-propyl)piperazin-1-yl]propyl}-3,4,9,10-perylenebis(dicarboximide)
  参考文献：
  名称：

  Cyclic perylene diimide: Selective ligand for tetraplex DNA binding over double stranded DNA

  摘要：

  Synthesized cyclic perylene diimide, cPDI, showed the binding constant of 6.3 x 10(6) M-1 with binding number of n = 2 with TA-core as a tetraplex DNA in 50 mM Tris-HCl buffer (pH = 7.4) containing 100 mM KCl using Schatchard analysis and showed a higher preference for tetraplex DNA than for double stranded DNA with over 10(3) times. CD spectra showed that TA-core induced its antiparallel conformation upon addition of cPDI in the absence or presence of K+ or Na+ ions. The cPDI inhibits the telomerase activity with IC50 of 0.3 mu M using TRAP assay which is potential anti-cancer drug with low side effect. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.10.014

文献信息

• Synthesis, characterization, optical and electrochemical properties of a new chiral multichromophoric system based on perylene and naphthalene diimides
  作者：Abimbola O. Aleshinloye、Jagadeesh B. Bodapati、Huriye Icil

  DOI：10.1016/j.jphotochem.2014.12.007

  日期：2015.3

  based on a perylene diimide chromophore consisting of two 1,4-bis(3-aminopropyl) piperazine linkers and two terminal chiral naphthalene bisimide chromophores has been synthesized. All of the chromophoric units are not π-conjugated with each other and could behave independently due to the presence of the nonconjugated linker. A new symmetrical dehydroabietyl substituted naphthalene diimide was also synthesized

  合成了一种基于a二酰亚胺生色团的新型手性和多发色大分子体系，该system团由两个1,4-双（3-氨基丙基）哌嗪连接基和两个末端手性萘双酰亚胺生色团组成。所有的发色单元都不彼此π共轭的，并且由于存在非共轭的接头而可以独立地表现。为了比较，还合成了新的对称的脱氢松香基取代的萘二酰亚胺。大分子和手性取代基被包括在大分子系统的外围位置，以增加溶解度并向分子间相互作用引入方向性。多发色大分子显示出新的和独特的光物理性质，不同于组分和共混物的单体态性质。由于较高的摩尔吸收系数，它在宽范围（320-600 nm）处显示出强吸收，并具有增强的光吸收。观察到，在溶液和固态中，大分子中分子间相互作用之间的吸收，发射和电化学特性是微妙的相互作用。在各种溶剂中都发现了光诱导的电子激发能转移，从能量收集的周边生色团到中心per核。发射和电化学特性在溶液和固态中都是大分子之间分子间相互作用的微妙相互作用。在各种溶剂
• Cyclic perylene diimide: Selective ligand for tetraplex DNA binding over double stranded DNA
  作者：Suresh Vasimalla、Shinobu Sato、Fuminori Takenaka、Yui Kurose、Shigeori Takenaka

  DOI：10.1016/j.bmc.2017.10.014

  日期：2017.12

  Synthesized cyclic perylene diimide, cPDI, showed the binding constant of 6.3 x 10(6) M-1 with binding number of n = 2 with TA-core as a tetraplex DNA in 50 mM Tris-HCl buffer (pH = 7.4) containing 100 mM KCl using Schatchard analysis and showed a higher preference for tetraplex DNA than for double stranded DNA with over 10(3) times. CD spectra showed that TA-core induced its antiparallel conformation upon addition of cPDI in the absence or presence of K+ or Na+ ions. The cPDI inhibits the telomerase activity with IC50 of 0.3 mu M using TRAP assay which is potential anti-cancer drug with low side effect. (C) 2017 Elsevier Ltd. All rights reserved.