5,6-dihydrodibenzoquinolizinium chloride | 138949-61-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 5,6-dihydrodibenzoquinolizinium chloride
• 英文别名: 5,6-Dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride
• CAS: 138949-61-8
• 化学式: C₁₇H₁₄N*Cl
• 分子量: 267.758
• InChiKey: UGEMUHDQYPRNSN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinoline 在 五氯化磷 作用下， 以 氯仿 为溶剂， 以52%的产率得到5,6-dihydrodibenzoquinolizinium chloride
  参考文献：
  名称：

  Structure-affinity relationships of berbines or 5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizines at α-adrenoceptors

  摘要：

  The synthesis of some derivatives of tetrahydro-8H-dibenzo[a,g]quinolizines or berbines is described. A pharmacological study was carried out at alpha-1 and alpha-2-adrenoceptors using radioligand binding techniques. This study has shown that the aromatic ring A is responsible for the alpha-2-affinity of berbines. Furthermore, the aromatic ring D is important for alpha-1-affinity. However, in this case, it seems that the planarity of the molecule is a very important structural parameter for affinity. The role of the nitrogen atom is also discussed. A conformational analysis of the partial saturated berbines was established by a C-13 NMR study.

  DOI：

  10.1016/0223-5234(91)90195-s

文献信息

• Merging C–H Vinylation with Switchable 6π-Electrocyclizations for Divergent Heterocycle Synthesis
  作者：Xunjin Jiang、Zhixiong Zeng、Yuhui Hua、Beibei Xu、Yang Shen、Jing Xiong、Huijuan Qiu、Yifan Wu、Tianhui Hu、Yandong Zhang

  DOI：10.1021/jacs.0c07680

  日期：2020.9.9

  Pyridinium-containing polyheterocycles exhibit distinctive biological properties, interesting electrochemical and optical properties, and thus are widely used as drugs, functional materials, and photocatalysts. Here, we describe a unified two-step strategy by merging Rh-catalyzed C-H vinylation with two switchable electrocyclizations, including aza-6π- and all-carbon 6π-electrocyclizations, for rapid

  含吡啶的多杂环具有独特的生物学特性、有趣的电化学和光学特性，因此被广泛用作药物、功能材料和光催化剂。在这里，我们通过将 Rh 催化的 CH 乙烯基化与两个可切换的电环化（包括 aza-6π- 和全碳 6π-电环化）合并来描述统一的两步策略，以快速和发散地获得二氢吡啶并异喹啉鎓和二氢苯并喹啉。通过计算，在适当的“HCl”源存在下，在热条件或光化学条件下，氮杂电环化的高选择性是由于前沿轨道的有利动力学和对称性造成的。
• CORALYNE ANALOGS AS TOPOISOMERASE INHIBITORS
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：EP0888346B1

  公开（公告）日：2001-06-06
• [EN] CORALYNE ANALOGS AS TOPOISOMERASE INHIBITORS<br/>[FR] ANALOGUES DE CORALYNE UTILES EN TANT QU'INHIBITEURS DE TOPOISOMERASE
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：WO1997029106A1

  公开（公告）日：1997-08-14

  (EN) The present invention provides protoberberine alkaloid derivatives useful as anticancer agents, and methods of use thereof. The invention also provides protoberberine derivatives useful as topoisomerase inhibitors. The invention further provides coralyne and nitidine derivatives which are topoisomerase I-targeted therapeutics effective against camptothecin resistant cancer cells, and are especially effective against CNS tumors.(FR) L'invention concerne des dérivés d'alcaloïde de protoberbérine utiles en tant qu'agents anti-cancer, ainsi que leurs procédés d'utilisation. Elle concerne également des dérivés de protoberbérine utiles en tant qu'inhibiteurs de topoisomérase. Elle concerne encore des dérivés de coralyne et de nitidine qui sont des agents thérapeutiques dirigés contre la topoisomérase I et efficaces contre les cellules cancéreuses résistant à la camptothécine, ainsi que, particulièrement, contre les tumeurs du système nerveux central.
• Structure-affinity relationships of berbines or 5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizines at α-adrenoceptors
  作者：G Memetzidis、JF Stambach、L Jung、C Schott、C Heitz、JC Stoclet

  DOI：10.1016/0223-5234(91)90195-s

  日期：1991.9

  The synthesis of some derivatives of tetrahydro-8H-dibenzo[a,g]quinolizines or berbines is described. A pharmacological study was carried out at alpha-1 and alpha-2-adrenoceptors using radioligand binding techniques. This study has shown that the aromatic ring A is responsible for the alpha-2-affinity of berbines. Furthermore, the aromatic ring D is important for alpha-1-affinity. However, in this case, it seems that the planarity of the molecule is a very important structural parameter for affinity. The role of the nitrogen atom is also discussed. A conformational analysis of the partial saturated berbines was established by a C-13 NMR study.