3-amino-4-[2-(phenyl)ethylamino]quinoline | 93547-68-3

• 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: 3-amino-4-[2-(phenyl)ethylamino]quinoline
• 英文别名: 4-N-(2-phenylethyl)quinoline-3,4-diamine
• CAS: 93547-68-3
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: UTVGCDOUIQIJRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-amino-4-[2-(phenyl)ethylamino]quinoline 在 过氧乙酸 、 氨 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-phenethyl-1H-imidazo[4,5-c]quinolin-4-amine
  参考文献：
  名称：

  Synthesis and Structure−Activity-Relationships of 1H-Imidazo[4,5-c]quinolines That Induce Interferon Production

  摘要：

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

  DOI：

  10.1021/jm049211v
• 作为产物：
  描述：

  4-Phenethylamino-3-nitro-chinolin 生成 3-amino-4-[2-(phenyl)ethylamino]quinoline
  参考文献：
  名称：

  1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents

  摘要：

  1H-咪唑并[4,5-c]喹啉是支气管扩张剂。描述了使用这些化合物作为支气管扩张剂的药理学方法，含有这些化合物的药物组合物，以及用于制备这些化合物的合成中间体。

  公开号：

  US04698348A1

文献信息

• 1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents
  申请人：Riker Laboratories, Inc.

  公开号：US04698348A1

  公开（公告）日：1987-10-06

  1H-imidazo[4,5-c]quinoline which are bronchodilators. Pharmacological methods of using the compounds as bronchodilators, pharmaceutical compositions containing the compounds, and synthetic intermediate for preparing the compounds are also described.

  1H-咪唑并[4,5-c]喹啉是支气管扩张剂。描述了使用这些化合物作为支气管扩张剂的药理学方法，含有这些化合物的药物组合物，以及用于制备这些化合物的合成中间体。
• 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
  申请人：Riker Laboratories, Inc.

  公开号：US04689338A1

  公开（公告）日：1987-08-25

  1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described.

  1H-咪唑并[4,5-c]喹啉-4-胺是抗病毒药物。还描述了使用这些化合物的药理学方法以及含有这些化合物的药物组合物。
• Heterocyclic-Modified Imidazoquinoline Derivatives: Selective TLR7 Agonist Regulates Tumor Microenvironment against Melanoma
  作者：Jiaxin Ou、Lu Zheng、Yanlin Chen、Qiuyue Fu、Liyi Tan、En Liang、Lan Huang、Yue Pan、Jiahua Ke、Zhipeng Chen、Kui Cheng

  DOI：10.1021/acs.jmedchem.3c01504

  日期：2024.3.14

  proinflammatory cytokines in murine dendritic cells, macrophages, and human peripheral blood mononuclear cells while promoting M1 macrophage polarization. In vivo studies using a B16-F10 mouse tumor model showed that SMU-L11 significantly enhanced immune cell activation and augmented CD4+ T and CD8+ T-cell proliferation, directly killing tumor cells and inhibiting tumor growth.

  针对 Toll 样受体 7 (TLR7) 的免疫疗法是一种有前景的癌症治疗策略。在此，我们描述了一系列基于咪唑喹啉的 TLR7 激动剂的设计和合成，并使用 HEK-Blue hTLR7 细胞评估 NF-κB 通路激活，以确定最有效的小分子 TLR7 激动剂SMU-L11 (EC 50 = 0.024 ± 0.002μM）。体外实验表明， SMU-L11特异性激活 TLR7，从而招募 MyD88 接头蛋白并激活 NF-κB 和 MAPK 信号通路。此外， SMU-L11被发现通过显着诱导小鼠树突状细胞、巨噬细胞和人外周血单核细胞分泌促炎细胞因子，同时促进M1巨噬细胞极化来发挥免疫增强作用。使用 B16-F10 小鼠肿瘤模型的体内研究表明， SMU-L11显着增强免疫细胞活化并增强 CD4 + T 和 CD8 + T 细胞增殖，直接杀死肿瘤细胞并抑制肿瘤生长。
• 1H-Imidazo[4,5-c]quinolines and 1H-imidazo[4,5-c]quinolin-4-amines
  申请人：RIKER LABORATORIES, INC.

  公开号：EP0145340B1

  公开（公告）日：1990-01-24
• Quinoline intermediates for the synthesis of 1H-imidazo[4,5-c]quinolines and 1H-imidazo[4,5-c]quinolin-4-amimes
  申请人：RIKER LABORATORIES, INC.

  公开号：EP0310950B1

  公开（公告）日：1993-01-13