8-methoxy-11H-pyrido<4,3-a>carbazole | 102852-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 8-methoxy-11H-pyrido<4,3-a>carbazole
• 英文别名: 8-methoxy-11H-pyrido[4,3-a]carbazole
• CAS: 102852-61-9
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: MSSBHBUMSIEEJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  isoquinolin-5-ylhydrazinium chloride 在 palladium on activated charcoal 硫酸 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 萘烷 为溶剂， 反应 8.75h， 生成 8-methoxy-11H-pyrido<4,3-a>carbazole
  参考文献：
  名称：

  Synthesis of 11H-pyridocarbazoles and derivatives. Comparison of their DNA binding and antitumor activity with those of 6H- and 7H-pyridocarbazoles

  摘要：

  The 8-methoxy- and 8-hydroxy-11H-pyrido[2,3-a]-, -[3,4-a]-, -[4,3-a]-, and [3,2-a]carbazoles were synthesized as potential DNA intercalating antitumor drugs. The structure of these compounds was confirmed by 1H NMR study including NOE experiments. The DNA binding properties of substituted and unsubstituted (8-H) heterocycles were determined by using their hydrochlorides or methiodides. These derivatives are able to bind to DNA with an affinity varying from 2.0 X 10(4) to 1.0 X 10(6) M-1, but most of them are unable to intercalate in contrast with the behavior of 6H- and 7H-pyridocarbazole analogues. The cytotoxicity of 11H-pyridocarbazoles, measured on L1210 cells in vitro, is much lower than those of 6H- and 7H-pyridocarbazole analogues.

  DOI：

  10.1021/jm00159a028

文献信息

• A Chemo- and Regioselective Tandem [3 + 2]Heteroannulation Strategy for Carbazole Synthesis: Combining Two Mechanistically Distinct Bond-Forming Processes
  作者：Emma Campbell、Andrea Taladriz-Sender、Olivia I. Paisley、Alan R. Kennedy、Jacob T. Bush、Glenn A. Burley

  DOI：10.1021/acs.joc.1c02943

  日期：2022.4.1

  A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald–Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is

  描述了通过顺序 [3 + 2] 异环化制备三环和四环咔唑的模块化方法。首先，建立了在一锅法中优化 Pd 催化的 Buchwald-Hartwig 胺化，然后进行 C/N-芳基化。其次，机械分析确定了化学和区域选择性顺序控制两个键形成步骤的起源。最后，通过制备一系列三环和四环咔唑来证明底物范围，包括方便地获得几种天然产物和抗癌剂。