6-amino-11-phenylbenzo[c]phenanthridine

• 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: 6-amino-11-phenylbenzo[c]phenanthridine
• 英文别名: 11-Phenylbenzo[c]phenanthridin-6-amine
• 化学式: C₂₃H₁₆N₂
• 分子量: 320.393
• InChiKey: XSQHYCUCRXGBKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-11-phenylbenzo[c]phenanthridine 、 苯乙烯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以69%的产率得到N-phenethyl-11-phenylbenzo[c]phenanthridine-6-amine
  参考文献：
  名称：

  苯乙烯与氨基杂芳烃的无过渡金属区域选择性氢化胺化

  摘要：

  已经描述了具有优异区域选择性的功能不同的苯乙烯与氨基取代的吡啶、喹啉、嘧啶、吡嗪和菲啶的碱介导的抗马尔科夫尼科夫加氢胺化。在仲胺上化学选择性地观察到双氢化胺化，而使伯胺保持完整。实验证据表明，所提出的反应涉及通过单电子转移将氨基吡啶基亲核加成到乙烯基芳烃上。

  DOI：

  10.1039/d2cc02781j
• 作为产物：
  描述：

  6-amino-11,12-dihydro-11-phenylbenzo[c]phenanthridine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以30%的产率得到6-amino-11-phenylbenzo[c]phenanthridine
  参考文献：
  名称：

  具有细胞抑制活性的苯并[c]菲啶衍生物的两步合成。

  摘要：

  DOI：

  10.1002/anie.200461969

文献信息

• A unified approach to benzo[<i>c</i>]phenanthridines <i>via</i> the cascade dual-annulation/formylation of 2-alkynyl/alkenylbenzonitriles
  作者：Shalini Verma、Manoj Kumar、Akhilesh K. Verma

  DOI：10.1039/d3cc00197k

  日期：——

  A base-mediated versatile cascade dual-annulation and formylation of 2-alkenyl/alkynylbenzonitriles with 2-methylbenzonitriles has been established for the construction of four different classes of amino and amido substituted benzo[c]phenanthridines and benzo[c]phenanthrolines. The synthesized molecules could be of utmost relevance in pharmaceuticals. The transformation uses the solvent DMF as the

  已经建立了碱基介导的多功能级联双环化和 2-烯基/炔基苯甲腈与 2-甲基苯甲腈的甲酰化，用于构建四种不同类别的氨基和酰氨基取代的苯并 [c] 菲啶和苯并 [c]菲咯啉。合成的分子可能在药物中具有最大的相关性。该转化使用溶剂 DMF 作为甲酰源，用于合成酰胺基取代的支架。这种无过渡金属的独特策略能够在室温下在一个锅中形成多个 C-C 和 C-N 键。
• Synthesis and Biological Evaluation of 11-Substituted 6-Aminobenzo[<i>c</i>]phenanthridine Derivatives, a New Class of Antitumor Agents
  作者：Ilka Kock、Dieter Heber、Matthias Weide、Ulrich Wolschendorf、Bernd Clement

  DOI：10.1021/jm0490888

  日期：2005.4.1

  The synthesis of 11-substituted 6-amino-11,12-dihydrobenzo[c]phenanthridines and 11-substituted 6-aminobenzo[c]phenanthridines through an efficient method is described. The antiproliferative activity of selected compounds against a wide panel of tumor cell lines was tested in the in vitro anticancer screening and the in vivo hollow fiber assay of the National Cancer Institute. Several compounds turned out to exhibit considerable cytotoxicity for tumor cells. For the study of structure-activity relationships different substituents were introduced in the 11-position. Compounds with methoxyphenyl substituents tended to show the highest potency. Several compounds exhibited noteworthy antitumor activity with GI(50) values across all cell lines < 1 mu M. 6-Amino-11-(3,4,5-trimethoxyphenyl)benzo [c] phenanthridine perchlorate was the most potent agent in the NCI's in vivo hollow fiber assay. Most of the tested compounds showed a remarkable selectivity for leukemia, breast cancer, and prostate cancer.
• A Two-Step Synthesis of Cytostatically Active Benzo[c]phenanthridine Derivatives
  作者：Bernd Clement、Matthias Weide、Ulrich Wolschendorf、Ilka Kock

  DOI：10.1002/anie.200461969

  日期：2005.1.14
• Transition-metal-free regioselective hydroamination of styrenes with amino-heteroarenes
  作者：Priyanka Meena、Ayushee、Monika Patel、Akhilesh K. Verma

  DOI：10.1039/d2cc02781j

  日期：——

  The base-mediated anti-Markovnikov hydroamination of functionally varied styrenes with amino-substituted pyridine, quinoline, pyrimidine, pyrazine, and phenanthridine with excellent regioselectivity has been described. Double hydroamination was observed chemoselectively on the secondary amine, leaving the primary amine intact. Experimental evidence suggests that the proposed reaction involves the nucleophilic

  已经描述了具有优异区域选择性的功能不同的苯乙烯与氨基取代的吡啶、喹啉、嘧啶、吡嗪和菲啶的碱介导的抗马尔科夫尼科夫加氢胺化。在仲胺上化学选择性地观察到双氢化胺化，而使伯胺保持完整。实验证据表明，所提出的反应涉及通过单电子转移将氨基吡啶基亲核加成到乙烯基芳烃上。