6-amino-9-(2,2-dimethoxyethyl)amino-2-ethoxy-5-p-nitrophenylazo-acridine | 1187548-70-4

• 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-9-(2,2-dimethoxyethyl)amino-2-ethoxy-5-p-nitrophenylazo-acridine
• 英文别名: 9-N-(2,2-dimethoxyethyl)-7-ethoxy-4-[(4-nitrophenyl)diazenyl]acridine-3,9-diamine
• CAS: 1187548-70-4
• 化学式: C₂₅H₂₆N₆O₅
• 分子量: 490.519
• InChiKey: YIHJGZPSIOLHDO-UHFFFAOYSA-N

物化性质

• 熔点：
  106-110 °C
• 沸点：
  746.3±60.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-amino-9-(2,2-dimethoxyethyl)amino-2-ethoxy-5-p-nitrophenylazo-acridine 在 三氟乙酸 作用下， 反应 15.0h， 以95%的产率得到9-amino-4-ethoxy-8-p-nitrophenylazo-7H-pyrido[4,3,2-kl]acridine
  参考文献：
  名称：

  Functionalization of the A ring of pyridoacridine as a route toward greater structural diversity. Synthesis of an octacyclic analogue of eilatin

  摘要：

  In an effort to increase the structural diversity of pyrido[4,3,2-kl] acridines, compounds containing amino substituents on the A ring were synthesized. The key-reactions involve regioselective electrophilic aromatic substitutions. The methodology was applied to the synthesis of the extended angular octacycle 8, which conjugates the physicochemical and spectroscopic properties of the pyridoacridine skeleton with the ability of [1,10] phenanthroline ring for metal complexation. The 9-aminopyridoacridine 4 displays significant cytostatic activities against two cancer cell lines, and may be considered as a new lead in the search of active derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.039
• 作为产物：
  描述：

  6-amino-9-(2,2-dimethoxyethyl)amino-2-ethoxy-acridine 、 4-nitrobenzenediazonium tetrafluoroborate 以 甲醇 为溶剂， 以86%的产率得到6-amino-9-(2,2-dimethoxyethyl)amino-2-ethoxy-5-p-nitrophenylazo-acridine
  参考文献：
  名称：

  Functionalization of the A ring of pyridoacridine as a route toward greater structural diversity. Synthesis of an octacyclic analogue of eilatin

  摘要：

  In an effort to increase the structural diversity of pyrido[4,3,2-kl] acridines, compounds containing amino substituents on the A ring were synthesized. The key-reactions involve regioselective electrophilic aromatic substitutions. The methodology was applied to the synthesis of the extended angular octacycle 8, which conjugates the physicochemical and spectroscopic properties of the pyridoacridine skeleton with the ability of [1,10] phenanthroline ring for metal complexation. The 9-aminopyridoacridine 4 displays significant cytostatic activities against two cancer cell lines, and may be considered as a new lead in the search of active derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.039

文献信息

• [EN] DIAZINYL AMINO ACRIDINES AND MEDICAL USES THEREOF<br/>[FR] DIAZINYL AMINO ACRIDINES ET LEURS UTILISATIONS MÉDICALES
  申请人：LARSSON LARS GUNNAR OLOF

  公开号：WO2019145375A1

  公开（公告）日：2019-08-01

  There is provided herein compounds of formula (I) and pharmaceutically-acceptable salts and/or detectably-labelled derivatives thereof, wherein R1 to R3, X, Y, n and m have meanings as provided in the description, together with formulations and products comprising the same. There is also provided the use of such compounds, formulations and products in the treatment of cancers characterised by increased MYC activity.

  本文提供了式（I）的化合物和药用盐和/或可检测标记衍生物，其中R1到R3、X、Y、n和m的含义如描述中所提供，以及包含这些化合物的配方和产品。还提供了这些化合物、配方和产品在治疗因MYC活性增加而特征化的癌症中的用途。
• DIAZINYL AMINO ACRIDINES AND MEDICAL USES THEREOF
  申请人：Larsson, Lars-Gunnar Olof

  公开号：EP3743409A1

  公开（公告）日：2020-12-02