6-amino-11,12-dihydro-11-(2-pyridyl)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-(2-pyridyl)benzo[c]phenanthridine
• 英文别名: 11-Pyridin-2-yl-11,12-dihydrobenzo[c]phenanthridin-6-amine
• 化学式: C₂₂H₁₇N₃
• 分子量: 323.397
• InChiKey: JWMOENWTBDJJSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-amino-11,12-dihydro-11-(2-pyridyl)benzo[c]phenanthridine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 高氯酸 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 以15%的产率得到6-amino-11-(2-pyridyl)benzo[c]phenanthridinium diperchlorate
  参考文献：
  名称：

  11-取代的苯并[c]菲啶：新结构及其抗增殖作用模式的认识

  摘要：

  的文库的各种新结构的合成11取代的6-氨基-11,12-二氢苯并[ c ^ ]菲啶（BP）和11-取代的6-氨基苯并[ C ^提出了]菲啶（BP-D）。描述了这些结构，进一步的合成修饰以及提供了约40种新衍生物的后续产品的制备。根据体外肿瘤细胞生长抑制的结果，通过比较NCI 60发育治疗计划（DTP）人类肿瘤细胞系筛选数据，研究了它们作为抗增殖药的潜力，其中包括迄今未发表的约40种癌症的化合物测试结果，多达60种癌症细胞系。NCI-COMPARE研究有助于提出高活性抗增殖药的作用方式。这些发现得到了体外生物学研究的支持，表明对微管蛋白聚合和解聚的抑制或对拓扑异构酶的抑制。加上候选药物的理化参数，结构-活动关系进行了严格讨论。微管蛋白相互作用或对拓扑异构酶I和IIα/β活性的抑制是两个原理，可以解释在NCI 60 DTP人肿瘤细胞系筛选中观察到的抗增殖活性。但是，也可以合理地假设这些化合物可

  DOI：

  10.1002/cmdc.201600199
• 作为产物：
  描述：

  吡啶-2-甲醛 、 邻甲基苯腈 在 potassium tert-butylate 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 生成 6-amino-11,12-dihydro-11-(2-pyridyl)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.
• 11-Substituted Benzo[<i>c</i>]phenanthridines: New Structures and Insight into Their Mode of Antiproliferative Action
  作者：Bernd Clement、Ulrich Girreser、Tamara N. Steinhauer、Christopher Meier、Doris Marko、Georg Aichinger、Ilka Kaltefleiter、Lars Stenzel、Dieter Heber、Matthias Weide、Ulrich Wolschendorf、Inga Zebothsen、Dana zur Nieden

  DOI：10.1002/cmdc.201600199

  日期：2016.10.6

  interaction or inhibition of topoisomerase I and IIα/β activity are two rationales that can explain the antiproliferative activity observed in the NCI 60 DTP human tumor cell line screen. However, it can also be reasonably assumed that these compounds address several targets, thus prohibiting the identification of simple structure–activity relationships. The new structures described herein are thought to act

  的文库的各种新结构的合成11取代的6-氨基-11,12-二氢苯并[ c ^ ]菲啶（BP）和11-取代的6-氨基苯并[ C ^提出了]菲啶（BP-D）。描述了这些结构，进一步的合成修饰以及提供了约40种新衍生物的后续产品的制备。根据体外肿瘤细胞生长抑制的结果，通过比较NCI 60发育治疗计划（DTP）人类肿瘤细胞系筛选数据，研究了它们作为抗增殖药的潜力，其中包括迄今未发表的约40种癌症的化合物测试结果，多达60种癌症细胞系。NCI-COMPARE研究有助于提出高活性抗增殖药的作用方式。这些发现得到了体外生物学研究的支持，表明对微管蛋白聚合和解聚的抑制或对拓扑异构酶的抑制。加上候选药物的理化参数，结构-活动关系进行了严格讨论。微管蛋白相互作用或对拓扑异构酶I和IIα/β活性的抑制是两个原理，可以解释在NCI 60 DTP人肿瘤细胞系筛选中观察到的抗增殖活性。但是，也可以合理地假设这些化合物可