N-(3-(4-(3-(acridin-9-ylamino)propyl)piperazin-1-yl)propyl)acridin-9-amine | 97614-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(3-(4-(3-(acridin-9-ylamino)propyl)piperazin-1-yl)propyl)acridin-9-amine
• 英文别名: N,N-bis(9-acridinyl)-1,4-bis(3-aminopropyl)piperazine；N1,N4-Di-9-acridinyl-1,4-piperazinedipropanamine；N-[3-[4-[3-(acridin-9-ylamino)propyl]piperazin-1-yl]propyl]acridin-9-amine
• CAS: 97614-84-1
• 化学式: C₃₆H₃₈N₆
• 分子量: 554.738
• InChiKey: AAMSBOZZFRTUFD-UHFFFAOYSA-N

物化性质

• 熔点：
  250-251 °C
• 沸点：
  808.6±65.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 9-phenoxyacridine 反应 0.5h， 以0.84 g的产率得到N-(3-(4-(3-(acridin-9-ylamino)propyl)piperazin-1-yl)propyl)acridin-9-amine
  参考文献：
  名称：

  单体和二聚吖啶化合物的合成作为阿尔茨海默病和朊病毒病的潜在治疗剂

  摘要：

  从取代的 9-氯吖啶开始，制备了一系列奎纳克林和间隔二聚吖啶化合物。使用基于 FACS 分析的快速筛选系统探索了它们中断朊病毒和阿尔茨海默特异蛋白与 Ab 肽的蛋白质结合的能力。双吖啶比相应的单体表现出更高的活性。在这些衍生物中，Aβ-肽的 2,4-二甲氧基-6-硝基化合物 7h 和 PrP 的 2-甲氧基-6-硝基化合物 7f 获得了最好的结果。

  DOI：

  10.1002/ardp.200900065

文献信息

• Potential antitumor agents. 44. Synthesis and antitumor activity of new classes of diacridines: importance of linker chain rigidity for DNA binding kinetics and biological activity
  作者：William A. Denny、Graham J. Atwell、Bruce C. Baguley、Laurence P. G. Wakelin

  DOI：10.1021/jm00149a005

  日期：1985.11

  Four classes of diacridines, joined at the 9-position by linker chains of varying length, rigidity, and polarity, were evaluated for DNA-binding properties and antitumor activity. Diacridines linked by flexible chains of varying polarity show relatively fast chromophore exchange kinetics among DNA binding sites but slower dissociation rates, suggesting the potential for considerable "creeping" of the drug along the helix, and are inactive in vivo. The exchange kinetics can be slowed dramatically by inclusion of positive charges in the side chain, but the resulting polycationic drugs are inactive in vivo, possibly due to poor distribution. Diacridines linked by a rigid, polar but neutral dicarbamoylpyrazole chain retain slow exchange kinetics, have a greatly reduced potential "creep rate", and possess good in vitro potency and significant in vivo antileukemic activity.
• Synthesis of Bis-acridine Derivatives Exhibiting Anticancer and Anti-inflammatory Activity
  作者：Sham M. Sondhi、Sandeep Kumar、Reshma Rani、Ajanta Chakraborty、Partha Roy

  DOI：10.1002/jhet.985

  日期：2013.3

  A series of bis‐acridine derivatives 3a–j and 5a–j have been synthesized by condensation of 9‐chloro‐2,4‐(un)substituted acridines (1a–e) and 9‐isothiocyanato‐2,4‐(un)substituted acridines (4a–e) with diamine 2a and 2b, respectively. These bis‐acridines were evaluated in vitro for activity against a panel of human cancer cell lines of lung (NCI H‐522), ovary (PA1), breast (T47D), colon (HCT‐15), and liver (HepG2). Several bis‐acridines were found to possess good anticancer activity against various cancer cell lines. Of these, compound 3h exhibited good anticancer activity against all cancer cell lines tested except liver (HepG2) cell line. In addition to this, these compounds were screened for anti‐inflammatory activity at a dose of 50 mg/kg p.o. Compound 3g exhibited 41% anti‐inflammatory activity, which is better than most commonly used standard drug ibuprofen, which showed 39% anti‐inflammatory (at 50 mg/kg p. o.) activity.
• Synthesis of Monomeric and Dimeric Acridine Compounds as Potential Therapeutics in Alzheimer and Prion Diseases
  作者：René Csuk、Alexander Barthel、Christian Raschke、Ralph Kluge、Dieter Ströhl、Lothar Trieschmann、Gerald Böhm

  DOI：10.1002/ardp.200900065

  日期：2009.12

  spacered dimeric acridine compounds was prepared. Their ability to interrupt the protein association of prion‐ and Alzheimer‐specific proteins and Ab peptides was explored using a fast screening system based on FACS analysis. The bis‐acridines displayed a higher activity than the corresponding monomers. Among these derivatives, best results were obtained with the 2,4‐dimethoxy‐6‐nitro compound 7h for

  从取代的 9-氯吖啶开始，制备了一系列奎纳克林和间隔二聚吖啶化合物。使用基于 FACS 分析的快速筛选系统探索了它们中断朊病毒和阿尔茨海默特异蛋白与 Ab 肽的蛋白质结合的能力。双吖啶比相应的单体表现出更高的活性。在这些衍生物中，Aβ-肽的 2,4-二甲氧基-6-硝基化合物 7h 和 PrP 的 2-甲氧基-6-硝基化合物 7f 获得了最好的结果。