1-dodecyl-2,3-dihydro-1H-imidazo[1,2-f]phenanthridin-4-ylium bromide

• 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: 1-dodecyl-2,3-dihydro-1H-imidazo[1,2-f]phenanthridin-4-ylium bromide
• 英文别名: 1-Dodecyl-2,3-dihydroimidazo[1,2-f]phenanthridin-4-ium;bromide
• 化学式: Br*C₂₇H₃₇N₂
• 分子量: 469.508
• InChiKey: PCMLTBKXPSUUSA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  7.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  菲啶 在 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 126.0h， 生成 1-dodecyl-2,3-dihydro-1H-imidazo[1,2-f]phenanthridin-4-ylium bromide
  参考文献：
  名称：

  Highly Stable Phenanthridinium Frameworks as a New Class of Tunable DNA Binding Agents with Cytotoxic Properties

  摘要：

  A new class of cytotoxic heteroaromatic cations is presented, based on the dihydro-imidazo-phenanthridinium framework (DIP), that have affinity for DNA and cytotoxicity toward cancerous cells. The DIP framework is particularly tunable due to the flexible synthetic methodology. Furthermore, the central moiety has proved to be very stable to hydrolysis and reduction compared to other phenanthridinium-based agents.

  DOI：

  10.1021/jm050320z

文献信息

• Phenanthridinium Derivatives as Dna Binding Agents
  申请人：Parenty Alexis

  公开号：US20070249652A1

  公开（公告）日：2007-10-25

  New classes of heterocyclic aromatic cationic compounds are disclosed, and in particular new classes of phenanthridinium derivatives, most notably dihydro-imidazo-phenanthridinium (DIP) compounds. These findings are based on the reaction of the middle b ring of a phenanthridinium core with primary amines to form DIP compounds (Formula A) or secondary amines to form 2-aminoalkyl phenanthridinium derivatives (Formula B). These reactions can also be applied to other classes of starting compounds which comprise a 6-membered ring aromatic heterocycle having a ring nitrogen and at least one alpha hydrogen atom which can be reacted with a primary or secondary amine.

  本文披露了一类新的杂环芳香阳离子化合物，特别是新的苯并咪唑苯并三氮杂环（DIP）化合物。这些发现基于苯并三氮杂环核心的中间b环与一级胺反应形成DIP化合物（公式A）或二级胺反应形成2-氨基烷基苯并三氮杂环衍生物（公式B）。这些反应也可以应用于其他类似的起始化合物，其包含一个具有环氮和至少一个α-氢原子的6元环芳香杂环，可以与一级或二级胺反应。
• PHENANTHRIDINIUM DERIVATIVES AS DNA BINDING AGENTS
  申请人：University Court of The University of Glasgow

  公开号：EP1692130A2

  公开（公告）日：2006-08-23
• US7947703B2
  申请人：——

  公开号：US7947703B2

  公开（公告）日：2011-05-24
• [EN] PHENANTHRIDINIUM DERIVATIVES AS DNA BINDING AGENTS<br/>[FR] COMPOSES AROMATIQUES HETEROCYCLIQUES
  申请人：UNIV GLASGOW

  公开号：WO2005054241A2

  公开（公告）日：2005-06-16

  New classes of heterocyclic aromatic cationic compounds are disclosed, and in particular new classes of phenanthridinium derivatives, most notably dihydro-imidazo-phenanthridinium (DIP) compounds. These findings are based on the reaction of the middle b ring of a phenanthridinium core with primary amines to form DIP compounds (Formula A) or secondary amines to form 2-aminoalkyl phenanthridinium derivatives (Formula B). These reactions can also be applied to other classes of starting compounds which comprise a 6-membered ring aromatic heterocycle having a ring nitrogen and at least one alpha hydrogen atom which can be reacted with a primary or secondary amine.