4-(9-吖啶基氨基)苯胺 | 58658-11-0

• 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
• 中文名称: 4-(9-吖啶基氨基)苯胺
• 英文名称: 9-(p-aminoanilino)acridine
• 英文别名: 4-(9-Acridinylamino)aniline；4-N-acridin-9-ylbenzene-1,4-diamine
• CAS: 58658-11-0
• 化学式: C₁₉H₁₅N₃
• 分子量: 285.348
• InChiKey: XTJBUPXVQDLXRF-UHFFFAOYSA-N

物化性质

• 沸点：
  487.5±25.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(9-吖啶基氨基)苯胺 在 sodium azide 、 sodium nitrite 作用下， 生成 9-(p-azidoanilino)acridine
  参考文献：
  名称：

  Identification of an acridine photoaffinity probe for trypanocidal action

  摘要：

  Twenty-four acridine derivatives were screened for trypanocidal activity in Trypanosoma brucei in order to determine which structural features of the acridine molecule confer maximal antiparasitic activity. The synthesis of several new azidoacridine derivatives are also reported as well as an assessment of their value as possible photoaffinity probes for the study of acridine trypanocidal action. The most effective and selective acridine trypanocides, with and without irradiation, were the 3-amino-10-methylacridinium salt derivatives. With brief irradiation, one azidoacridine, 3-amino-6-azido-10-methylacridinium chloride, showed considerable trypanocidal activity at very limiting drug concentrations (10(-7)M) and warrants consideration as a possible photoaffinity probe.

  DOI：

  10.1021/jm00373a010
• 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 4-(9-吖啶基氨基)苯胺
  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

• Development of acridine derivatives as selective Mycobacterium tuberculosis DNA gyrase inhibitors
  作者：Brahmam Medapi、Nikhila Meda、Pushkar Kulkarni、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2016.01.011

  日期：2016.2

  quinoline–aminopiperidine hybrid MTB DNA gyrase inhibitors with aiming more potency and less cardiotoxicity. We synthesized thirty six compounds using four step synthesis from 2-chloro benzoic acid. Among them compound 4-chloro-N-(4-((2-methylacridin-9-yl)amino)phenyl)benzenesulphonamide (6) was found to be more potent with MTB DNA gyrase super coiling IC50 of 5.21 ± 0.51 μM; MTB MIC of 6.59 μM and no zHERG cardiotoxicity

  在这项研究中，我们从较早报道的喹啉-氨基哌啶杂化MTB DNA促旋酶抑制剂中设计了对苯二胺连接的a啶衍生物，其目的是提高药效和降低心脏毒性。我们使用2-氯苯甲酸四步合成法合成了36种化合物。其中化合物4-氯-N-（4-（（（2-甲基rid啶-9-基）氨基）苯基）苯磺酰胺（6）用MTB DNA促旋酶超级卷曲IC 50为5.21±0.51μM更有效。对小鼠巨噬细胞系RAW 264.7的MTB MIC为6.59μM，在30μM时无zHERG心脏毒性，在50μM时无11.78％的抑制作用。
• [EN] NOVEL HDMX INHIBITORS AND THEIR USE FOR CANCER TREATMENT<br/>[FR] NOUVEAUX INHIBITEURS HDMX ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：MIRX PHARMACEUTICALS LLC

  公开号：WO2015153535A1

  公开（公告）日：2015-10-08

  The present invention provides for novel acridine-like class of compounds that have demonstrated efficiency in treating cancer. The compounds of the present invention have demonstrated efficacy in binding to and antagonizing the activity of the p53 repressor, HDMX. Once administered to a cell, the compounds of the present invention bind HDMX, thereby allowing p53 to induce apoptosis of the cancerous cell. A combination of this class of compounds along with Nutlin3 provides a novel approach to treat cancers.

  本发明提供了一种新型的类似于吖啶的化合物，已经证明可以有效地治疗癌症。本发明的化合物已经证明在结合并拮抗p53抑制剂HDMX的活性方面具有疗效。一旦这些化合物被注入细胞，它们会与HDMX结合，从而使p53诱导癌细胞凋亡。将这类化合物与Nutlin3结合使用可以提供一种治疗癌症的新方法。
• HDMX inhibitors and their use for cancer treatment
  申请人：MIRX PHARMACEUTICALS, LLC

  公开号：US10183912B2

  公开（公告）日：2019-01-22

  The present invention provides for novel acridine-like class of compounds that have demonstrated efficiency in treating cancer. The compounds of the present invention have demonstrated efficacy in binding to and antagonizing the activity of the p53 repressor, HDMX. Once administered to a cell, the compounds of the present invention bind HDMX, thereby allowing p53 to induce apoptosis of the cancerous cell. A combination of this class of compounds along with Nutlin3 provides a novel approach to treat cancers.

  本发明提供了新型吖啶类化合物，这些化合物已证明可有效治疗癌症。本发明的化合物在与 p53 抑制剂 HDMX 结合并拮抗其活性方面具有显著疗效。一旦给细胞用药，本发明的化合物就会与 HDMX 结合，从而使 p53 能够诱导癌细胞凋亡。这类化合物与 Nutlin3 的结合提供了一种治疗癌症的新方法。
• NOVEL HDMX INHIBITORS AND THEIR USE FOR CANCER TREATMENT
  申请人：MIRX PHARMACEUTICALS, LLC

  公开号：US20170022166A1

  公开（公告）日：2017-01-26

  The present invention provides for novel acridine-like class of compounds that have demonstrated efficiency in treating cancer. The compounds of the present invention have demonstrated efficacy in binding to and antagonizing the activity of the p53 repressor, HDMX. Once administered to a cell, the compounds of the present invention bind HDMX, thereby allowing p53 to induce apoptosis of the cancerous cell. A combination of this class of compounds along with Nutlin3 provides a novel approach to treat cancers.
• Identification of an acridine photoaffinity probe for trypanocidal action
  作者：William J. Firth、Andrew Messa、Robert Reid、Rung Chou Wang、Charles L. Watkins、Lerena W. Yielding

  DOI：10.1021/jm00373a010

  日期：1984.7

  Twenty-four acridine derivatives were screened for trypanocidal activity in Trypanosoma brucei in order to determine which structural features of the acridine molecule confer maximal antiparasitic activity. The synthesis of several new azidoacridine derivatives are also reported as well as an assessment of their value as possible photoaffinity probes for the study of acridine trypanocidal action. The most effective and selective acridine trypanocides, with and without irradiation, were the 3-amino-10-methylacridinium salt derivatives. With brief irradiation, one azidoacridine, 3-amino-6-azido-10-methylacridinium chloride, showed considerable trypanocidal activity at very limiting drug concentrations (10(-7)M) and warrants consideration as a possible photoaffinity probe.