6-amino-11-(4-methylphenyl)benzo[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-(4-methylphenyl)benzo[c]phenanthridine
• 英文别名: 11-(4-Methylphenyl)benzo[c]phenanthridin-6-amine
• 化学式: C₂₄H₁₈N₂
• 分子量: 334.42
• InChiKey: KAWMPYDNGGZZDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-amino-11,12-dihydro-11-(4-methylphenyl)benzo[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 12.0h， 生成 6-amino-11-(4-methylphenyl)benzo[c]phenanthridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 11-Substituted 6-Aminobenzo[c]phenanthridine Derivatives, a New Class of Antitumor Agents

  摘要：

  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.

  DOI：

  10.1021/jm0490888

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.