acridin-9-yl-(4-methoxyphenyl)-amine | 61421-82-7

• 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: acridin-9-yl-(4-methoxyphenyl)-amine
• 英文别名: N-(4-methoxyphenyl)acridin-9-amine；acridin-9-yl-(4-methoxy-phenyl)-amine；Acridin-9-yl-(4-methoxy-phenyl)-amin；ACRIDINE, 9-(p-ANISIDINO)-
• CAS: 61421-82-7
• 化学式: C₂₀H₁₆N₂O
• mdl: MFCD00399091
• 分子量: 300.36
• InChiKey: QQQZGKVRDOCMAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 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：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acridin-9-yl-(4-methoxyphenyl)-amine 在 ammonium hydroxide 、 硫化氢 作用下， 生成 acridine-9-thione
  参考文献：
  名称：

  Asquith et al., Journal of the Chemical Society, 1948, p. 1181

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 盐酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 为溶剂， 反应 6.0h， 生成 acridin-9-yl-(4-methoxyphenyl)-amine
  参考文献：
  名称：

  发现基于吖啶的 LSD1 抑制剂作为针对胃癌 LSD1 的免疫激活剂

  摘要：

  LSD1在多种癌症中过表达，促进肿瘤细胞增殖、肿瘤扩张，抑制免疫细胞浸润，与免疫检查点抑制剂治疗密切相关。因此，抑制 LSD1 已被认为是一种有前途的癌症治疗策略。在这项研究中，我们筛选了一个针对 LSD1 的内部小分子库，LSD1 是 FDA 批准的治疗急性白血病和恶性淋巴瘤的药物安吖啶，被发现表现出中等的抗 LSD1 抑制活性（IC 50 = 0.88 μM ）  。通过进一步的药物化学研究，活性最强的化合物显着提高了 6 倍的抗 LSD1 活性（IC 50 = 0.073 微米）。进一步的机制研究表明，化合物 6x 抑制胃癌细胞的干性和迁移，并降低 BGC-823 和 MFC 细胞中 PD-L1（程序性细胞死亡配体 1）的表达。更重要的是，当用化合物 6x 处理时，BGC-823 细胞更容易被 T 细胞杀死。此外，化合物 6x 在小鼠中也抑制了肿瘤生长。总而言之，我们的研究结果表明，基于吖啶的新型

  DOI：

  10.1016/j.ejmech.2023.115255

文献信息

• Design, synthesis and biological evaluation of novel acridine and quinoline derivatives as tubulin polymerization inhibitors with anticancer activities
  作者：Yichang Ren、Yong Ruan、Binbin Cheng、Ling Li、Jin Liu、Yuyu Fang、Jianjun Chen

  DOI：10.1016/j.bmc.2021.116376

  日期：2021.9

  A series of acridine and quinoline derivatives were designed and synthesized based on our previous work as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 3b exhibited the highest antiproliferative activity with an IC50 of 261 nM against HepG-2 cells (the most sensitive cell line). In addition, compound 3b was able to suppress the formation of HepG-2 colonies. Mechanism

  一系列吖啶和喹啉衍生物是基于我们之前的工作设计和合成的，它们是针对秋水仙碱结合位点的新型微管蛋白抑制剂。其中，化合物3b对HepG-2细胞（最敏感的细胞系）表现出最高的抗增殖活性，IC 50为261 nM。此外，化合物3b能够抑制 HepG-2 集落的形成。机制研究表明，化合物3b在体外有效抑制微管蛋白聚合并破坏 HepG-2 细胞中的微管动力学。此外，化合物3b以剂量依赖性方式抑制癌细胞的迁移。此外，化合物3b诱导细胞周期停滞在 G2/M 期并导致细胞凋亡。最后，对接研究表明，化合物3b与微管蛋白的秋水仙碱结合位点非常吻合，并与 CA-4 重叠良好。总的来说，这些结果表明化合物3b是一种值得进一步研究的新型微管蛋白抑制剂。
• MATRIX FOR MALDI MASS SPECTROMETRY AND MALDIMASS SPECTROMETRY METHOD
  申请人：Shindo Mitsuru

  公开号：US20140151548A1

  公开（公告）日：2014-06-05

  Provided is a matrix for MALDI mass spectrometry that has a high ability of ionizing low-molecular-weight compounds, and makes it possible to make measurement in a negative ion mode. The matrix is a matrix for mass spectrometry that contains one or more compounds selected from the group consisting of compounds each represented by the following general formula (I), (II) or (III), and their salts thereof. In the formulae (I), (II) and (III), X and Z are each C or N; R 1 and R 5 are each selected from the group consisting of H, an alkyl group, a (substituted) aryl group, a (substituted) arylalkyl group, and a (substituted) heteroaryl group; R 2 and R 6 are each selected from the group consisting of H, an alkyl group, an alkoxyl group, an amino group, a halogen atom, a nitro group, an allyl group, a (substituted) aryl group, and a (substituted) heteroaryl group; and R 7 and R 8 are each selected from the group consisting of H and an amino group provided that a case where R 1 =R 2 =H, and a case where R 7 =R 8 =an amino group are excluded.

  提供的是一种用于MALDI质谱的矩阵，具有高能力电离低分子量化合物的能力，并使得在负离子模式下进行测量成为可能。该矩阵是一种质谱矩阵，包含从由以下通式（I）、（II）或（III）表示的化合物组成的化合物中选择的一个或多个化合物及其盐。在式（I）、（II）和（III）中，X和Z分别为C或N；R1和R5分别选择自H、烷基、（取代）芳基、（取代）芳基烷基和（取代）杂芳基组成的群；R2和R6分别选择自H、烷基、烷氧基、氨基、卤素原子、硝基、烯丙基、（取代）芳基和（取代）杂芳基组成的群；R7和R8分别选择自H和氨基，但排除R1=R2=H和R7=R8=氨基的情况。
• MATRIX FOR MALDI MASS SPECTROMETRY
  申请人：Kyushu University National University Corporation

  公开号：EP2730918A1

  公开（公告）日：2014-05-14

  Provided is a matrix for MALDI mass spectrometry that has a high ability of ionizing low-molecular-weight compounds, and makes it possible to make measurement in a negative ion mode. The matrix is a matrix for mass spectrometry that contains one or more compounds selected from the group consisting of compounds each represented by the following general formula (I), (II) or (III), and their salts thereof. In the formulae (I), (II) and (III), X and Z are each C or N; R1 and R5 are each selected from the group consisting of H, an alkyl group, a (substituted) aryl group, a (substituted) arylalkyl group, and a (substituted) heteroaryl group; R2 and R6 are each selected from the group consisting of H, an alkyl group, an alkoxyl group, an amino group, a halogen atom, a nitro group, an allyl group, a (substituted) aryl group, and a (substituted) heteroaryl group; and R7 and R8 are each selected from the group consisting of H and an amino group provided that a case where R1 = R2 = H, and a case where R7 = R8 = an amino group are excluded.

  本发明提供了一种用于 MALDI 质谱分析的基质，该基质对低分子量化合物具有较高的电离能力，并可在负离子模式下进行测量。该基质是一种用于质谱分析的基质，含有一种或多种选自以下通式 (I)、(II) 或 (III) 所代表的化合物及其盐类的化合物。在式(I)、(II)和(III)中，X 和 Z 各自为 C 或 N；R1 和 R5 各自选自由 H、烷基、（取代的）芳基、（取代的）芳烷基和（取代的）杂芳基组成的组；R2和R6各自选自由H、烷基、烷氧基、氨基、卤素原子、硝基、烯丙基、（取代的）芳基和（取代的）杂芳基组成的组；以及R7和R8各自选自由H和氨基组成的组，但不包括R1＝R2＝H的情况和R7＝R8＝氨基的情况。
• Synthesis and SAR study of acridine, 2-methylquinoline and 2-phenylquinazoline analogues as anti-prion agents
  作者：H. Cope、R. Mutter、W. Heal、C. Pascoe、P. Brown、S. Pratt、B. Chen

  DOI：10.1016/j.ejmech.2006.05.002

  日期：2006.10

  Transmissible spongiform encephalopathies (TSEs) are thought to arise from aggregation of a protease resistant protein denoted PrPSc, which is a misfolded isoform of the normal cellular prion protein PrPC. Using virtual high-throughput screening we have selected structures analogous to acridine, 2-methyquinoline and 2-phenylquinazoline as potential therapeutic candidates for the treatment of TSEs. From the synthesis and screening of constructed libraries we have shown that an electron-rich aromatic ring attached through an amine linker to the position para to the ring nitrogen is beneficial to both binding to PrPC and the suppression of PrPSc accumulation for acridine and 2-methylquinoline analogues. 2-Phenylquinazoline analogues appear to utilise a different mode of action by binding at a different location and/or pose. We report IC(50)s in the nanomolar range. (c) 2006 Elsevier Masson SAS. All rights reserved.
• 144. N-substituted 5-aminoacridines
  作者：D. J. Dupré、F. A. Robinson

  DOI：10.1039/jr9450000549

  日期：——