4,4'-Bis(9-acridinyl)-octamethylenediamin | 57780-57-1

• 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: 4,4'-Bis(9-acridinyl)-octamethylenediamin
• 英文别名: N,N'-Bis-9-acridino-octamethylendiamin；N,N-bis(9-acridinyl)-1,8-octanediamine；NSC 219734；Acridine, 9,9'-octamethylenedi(imino)bis-；N,N'-di(acridin-9-yl)octane-1,8-diamine
• CAS: 57780-57-1
• 化学式: C₃₄H₃₄N₄
• 分子量: 498.671
• InChiKey: NEAXIRVWYPBDID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-Bis(9-acridinyl)-octamethylenediamin 以80%的产率得到
  参考文献：
  名称：

  SINGH A. K., CHEM. AND PHARM. BULL. , 1975, 23, NO 8, 1869-1873

  摘要：

  DOI：
• 作为产物：
  描述：

  9-氯吖啶 、 1,8-辛二胺 在 苯酚 作用下， 生成 4,4'-Bis(9-acridinyl)-octamethylenediamin
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00149a005

文献信息

• 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。
• DENNY, W. A.;ATWELL, G. J.;BAGULEY, B. C.;WAKALIN, L. P. G., J. MED. CHEM., 1985, 28, N 11, 1568-1574
  作者：DENNY, W. A.、ATWELL, G. J.、BAGULEY, B. C.、WAKALIN, L. P. G.

  DOI：——

  日期：——
• METHODS AND COMPOUNDS FOR REGULATING APOPTOSIS
  申请人：Reed John C.

  公开号：US20090118135A1

  公开（公告）日：2009-05-07

  An assay for determining compounds that inhibit activity of a BCl-2 protein, or affect conversion of Bcl-2 from an antiapoptotic to a proapoptotic form are described. In addition, compounds that modulate the function of anti-apoptotic proteins such as Bcl-2 and related Bcl-2 family members are identified.
• 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.
• SINGH A. K., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 8, 1869-1873
  作者：SINGH A. K.

  DOI：——

  日期：——