4-((6-chloro-2-methoxyacridin-9-yl)amino)phenol | 5409-67-6

• 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: 4-((6-chloro-2-methoxyacridin-9-yl)amino)phenol
• 英文别名: 4-(6-chloro-2-methoxy-acridin-9-ylamino)-phenol；4-(6-Chlor-2-methoxy-acridin-9-ylamino)-phenol；4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenol
• CAS: 5409-67-6
• 化学式: C₂₀H₁₅ClN₂O₂
• 分子量: 350.804
• InChiKey: SAEIEYREYSNRQA-UHFFFAOYSA-N

物化性质

• 熔点：
  266 °C (decomp)
• 沸点：
  524.5±45.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((6-chloro-2-methoxyacridin-9-yl)amino)phenol 在 四氢吡咯 、 聚合甲醛 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 以38%的产率得到6-chloro-2-methoxyacridone
  参考文献：
  名称：

  Pyronaridine Protects against SARS-CoV-2 Infection in Mouse

  摘要：

  DOI：

  10.1021/acsinfecdis.2c00091
• 作为产物：
  描述：

  6,9-二氯-2-甲氧基吖啶 、 4-氨基苯酚盐酸盐 在 水 作用下， 生成 4-((6-chloro-2-methoxyacridin-9-yl)amino)phenol
  参考文献：
  名称：

  氨基烷基酚作为抗疟药（杂环氨基）-α-氨基-邻甲酚；迷彩的合成。

  摘要：

  DOI：

  10.1021/ja01184a023

文献信息

• [EN] TARGETING DNA REPAIR IN TUMOR CELLS VIA INHIBITION OF ERCC1-XPF<br/>[FR] CIBLAGE DE LA RÉPARATION DE L'ADN DANS DES CELLULES TUMORALES PAR INHIBITION D'ERCC1-XPF
  申请人：UNIV ALBERTA

  公开号：WO2020248075A9

  公开（公告）日：2021-10-21
• Stawrowskaja, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 193,197;engl.Ausg.S.177,180
  作者：Stawrowskaja

  DOI：——

  日期：——
• Stawrowskaja, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 821,823; engl. Ausg. S. 787, 789
  作者：Stawrowskaja

  DOI：——

  日期：——
• Targeting DNA Repair in Tumor Cells via Inhibition of ERCC1–XPF
  作者：Ahmed H. Elmenoufy、Francesco Gentile、David Jay、Feridoun Karimi-Busheri、Xiaoyan Yang、Olivier M. Soueidan、Claudia Weilbeer、Rajam S. Mani、Khaled H. Barakat、Jack A. Tuszynski、Michael Weinfeld、Frederick G. West

  DOI：10.1021/acs.jmedchem.9b00326

  日期：2019.9.12

  The ERCC1-XPF heterodimer is a 5'-3' structure-specific endonuclease, which plays an essential role in several DNA repair pathways in mammalian cells. ERCC1-XPF is primarily involved in the repair of chemically induced helix distorting and bulky DNA lesions, such as cyclobutane pyrimidine dimers (CPDs), and DNA interstrand cross-links. Inhibition of ERCC1-XPF has been shown to potentiate cytotoxicity of platinum-based drugs and cyclophosphamide in cancer cells. In this study, the previously described ERCC1-XPF inhibitor 4-((6-chloro-2-methoxyacridin-9-yl)amino)-2-((4-methylpiperazin-1-yl)methyl)phenol (compound 1) was used as a reference compound. Following the outcome of docking-based virtual screening (VS), we synthesized seven novel derivatives of 1 that were identified in silico as being likely to have high binding affinity for the ERCC1-XPF heterodimerization interface by interacting with the XPF double helix hairpin helix (HhH2) domain. Two of the new compounds, 4-((6-chloro-2-methoxyacridin-9-yl)amino)-2-((4-cyclohexylpiperazin-1-yl)methyl)-phenol (compound 3) and 4-((6-chloro-2-methoxyacridin-9-yl)amino)-24(4-(2-(dimethylamino)ethyl) piperazin-1-yl) methyl) phenol (compound 4), were shown to be potent inhibitors of ERCC1-XPF activity in vitro. Compound 4 showed significant inhibition of the removal of CPDs in UV-irradiated cells and the capacity to sensitize colorectal cancer cells to UV radiation and cyclophosphamide.
• Aminoalkylphenols as Antimalarials. II.¹ (Heterocyclic-amino)-α-amino-o-cresols. The Synthesis of Camoquin²
  作者：J. H. Burckhalter、F. H. Tendick、Eldon M. Jones、Patricia A. Jones、W. F. Holcomb、A. L. Rawlins

  DOI：10.1021/ja01184a023

  日期：1948.4