6-amino-11,12-dihydro-11-(2,3,4-trimethoxyphenyl)benzo[c]phenanthridine | 420834-63-5

• 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-(2,3,4-trimethoxyphenyl)benzo[c]phenanthridine
• 英文别名: 11-(2,3,4-Trimethoxyphenyl)-11,12-dihydrobenzo[c]phenanthridin-6-amine
• CAS: 420834-63-5
• 化学式: C₂₆H₂₄N₂O₃
• 分子量: 412.488
• InChiKey: HRSAZIXAEDARCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-11,12-dihydro-11-(2,3,4-trimethoxyphenyl)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-(2,3,4-Trimethoxyphenyl)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：

  邻甲基苯腈 、 2,3,4-三甲氧基苯甲醛 在 potassium tert-butylate 作用下， 以 various solvent(s) 为溶剂， 生成 6-amino-11,12-dihydro-11-(2,3,4-trimethoxyphenyl)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

• PHENANTHRIDINE DERIVATIVES AND ANTITUMORAL MEDICAMENTS CONTAINING PHENANTHRIDINE
  申请人：——

  公开号：US20040034051A1

  公开（公告）日：2004-02-19

  The invention relates to novel phenanthridine derivatives and to medicaments, which are for use in antitumoral therapy and prophylaxis and which contain these phenanthridine derivatives. It could be shown that up to now specifically substituted phenanthridine derivatives of the prior art neither have a known nor an antitumoral activity that is to be expected.

  本发明涉及新型菲啶衍生物以及用于抗肿瘤治疗和预防并含有这些菲啶衍生物的药物。迄今为止，现有技术中的特异性取代菲啶衍生物既不具有已知的抗肿瘤活性，也不具有预期的抗肿瘤活性。
• PHENANTHRIDINDERIVATE UND PHENANTHRIDIN ENTHALTENDE ANTITUMORALE ARZNEIMITTEL
  申请人：Clement, Bernd

  公开号：EP1334115B1

  公开（公告）日：2007-05-16
• US6747038B2
  申请人：——

  公开号：US6747038B2

  公开（公告）日：2004-06-08