6-amino-11,12-dihydro-11-(3,4-methylenedioxyphenyl)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-11,12-dihydro-11-(3,4-methylenedioxyphenyl)benzo[c]phenanthridine
• 英文别名: 11-(1,3-Benzodioxol-5-yl)-11,12-dihydrobenzo[c]phenanthridin-6-amine
• 化学式: C₂₄H₁₈N₂O₂
• 分子量: 366.419
• InChiKey: PTDNYUYZIKJQHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-11,12-dihydro-11-(3,4-methylenedioxyphenyl)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 11-(1,3-Benzodioxol-5-yl)benzo[c]phenanthridin-6-amine
  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
• 作为产物：
  描述：

  胡椒醛 、 邻甲基苯腈 在 potassium tert-butylate 作用下， 以 various solvent(s) 为溶剂， 生成 6-amino-11,12-dihydro-11-(3,4-methylenedioxyphenyl)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

• 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.