1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine

• 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: 1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine
• 英文别名: 1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine；1-benzylimidazo[4,5-c]quinolin-4-amine
• 化学式: C₁₇H₁₄N₄
• 分子量: 274.325
• InChiKey: ZPVABWKMDUVERV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine 、 叔丁氧羰酰基肌氨酸 在 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以74.1%的产率得到tert-butoxycarbonyl-1-benzyl-1H-imidazo[4,5-c]quinolin-4-sarcosine
  参考文献：
  名称：

  1H-咪唑并[4,5-c]喹啉-4-胺类及其相关化合 物的前药

  摘要：

  本发明涉及具有通式1“结构式1”或通式2“结构式2”的1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物的前药的设计与合成，其可由1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物与适当的乙酸酐或乙酰氯反应制得。实验结果表明超过90％的前药能在几分钟内回到母药结构，可用于治疗人或动物的任何1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物可治疗的状态，避免1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物所产生的大多数副作用。通过前药的控释透皮给药系统可使血液中1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物的浓度稳定在最佳的治疗浓度，提升疗效并减少副作用。

  公开号：

  CN106432226B
• 作为产物：
  描述：

  N⁴-benzylquinoline-3,4-diamine 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-phenylmethyl-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

文献信息

• 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。
• 1H-imidazo\x9b4,5-c!quinolin-4-amines
  申请人：Riker Laboratories, Inc.

  公开号：US05756747A1

  公开（公告）日：1998-05-26

  Novel 1H-imidazo\x9b4,5-c!quinolin-4-amines are disclosed. The compounds function as antiviral agents and they are potential synthetic intermediates in the preparation of known antiviral agents and labeled known antiviral agents. Processes for the preparation of the compounds, methods for their antiviral use, and methods of inducing interferon biosynthesis, are also described.

  本文披露了1H-咪唑[4,5-c]喹啉-4-胺类新型化合物。这些化合物可作为抗病毒药物，并且它们是已知抗病毒药物和标记已知抗病毒药物制备中的潜在合成中间体。本文还描述了制备这些化合物的方法，它们的抗病毒用途的方法以及诱导干扰素生物合成的方法。
• 1H-咪唑并[4,5-c]喹啉-4-胺类及其相关化合 物的前药
  申请人：于崇曦

  公开号：CN106432226B

  公开（公告）日：2019-08-30

  本发明涉及具有通式1“结构式1”或通式2“结构式2”的1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物的前药的设计与合成，其可由1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物与适当的乙酸酐或乙酰氯反应制得。实验结果表明超过90％的前药能在几分钟内回到母药结构，可用于治疗人或动物的任何1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物可治疗的状态，避免1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物所产生的大多数副作用。通过前药的控释透皮给药系统可使血液中1H‑咪唑并[4,5‑c]喹啉‑4‑胺类及其相关化合物的浓度稳定在最佳的治疗浓度，提升疗效并减少副作用。
• HIGH PENETRATION PRODRUG COMPOSITIONS OF 1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES AND 1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINE-RELATED COMPOUNDS
  申请人：YU Chongxi

  公开号：US20100021394A1

  公开（公告）日：2010-01-28

  The invention provides compositions of novel high penetration compositions (HPC) or high penetration prodrugs (HPP) of 1H-imidazo[4,5-c]quinolin-4-amines and 1H-imidazo[4,5-c]quinolin-4-amine-related compounds, which are capable of crossing biological barriers with high penetration efficiency. The HPPs are capable of being converted to parent active drugs or drug metabolites after crossing the biological barrier and thus can render treatments for the conditions that the parent drugs or metabolites can. Additionally, the HPPs are capable of reaching areas that parent drugs may not be able to access or to render a sufficient concentration at the target areas and therefore render novel treatments. The HPPs can be administered to a subject through various administration routes, e.g., locally delivered to an action site of a condition with a high concentration or systematically administered to a biological subject and enter the general circulation with a faster rate.

  本发明提供了一种新型高穿透力化合物（HPC）或高穿透力前药（HPP）的组合物，其中包括1H-咪唑[4,5-c]喹啉-4-胺和1H-咪唑[4,5-c]喹啉-4-胺相关化合物。这些化合物能够高效地穿过生物屏障。HPP可以在穿过生物屏障后被转化为原始活性药物或药物代谢物，从而可以治疗与原始药物或代谢物相关的疾病。此外，HPP能够到达原始药物无法接触到或无法在目标区域产生足够浓度的区域，从而提供新型治疗方法。HPP可以通过各种给药途径给予受试者，例如在治疗区域局部给药以高浓度作用或系统性给药给生物受试者，并以更快的速度进入全身循环。
• High penetration prodrug compositions of 1H-imidazo[4,5-C]quinolin-4-amines and 1H-imidazo[4,5-C]quinolin-4-amine-related compounds
  申请人：——

  公开号：US08349866B2

  公开（公告）日：2013-01-08

  The invention provides compositions of novel high penetration compositions (HPC) or high penetration prodrugs (HPP) of 1H-imidazo[4,5-c]quinolin-4-amines and 1H-imidazo[4,5-c]quinolin-4-amine-related compounds, which are capable of crossing biological barriers with high penetration efficiency. The HPPs are capable of being converted to parent active drugs or drug metabolites after crossing the biological barrier and thus can render treatments for the conditions that the parent drugs or metabolites can. Additionally, the HPPs are capable of reaching areas that parent drugs may not be able to access or to render a sufficient concentration at the target areas and therefore render novel treatments. The HPPs can be administered to a subject through various administration routes, e.g., locally delivered to an action site of a condition with a high concentration or systematically administered to a biological subject and enter the general circulation with a faster rate.

  本发明提供了1H-咪唑[4,5-c]喹啉-4-胺及其相关化合物的新型高渗透组成物（HPC）或高渗透前药（HPP），能够高效地穿过生物屏障。HPP能够在穿过生物屏障后转化为母药或药物代谢产物，从而可以治疗母药或代谢产物所能治疗的疾病。此外，HPP能够到达母药无法到达的区域或者在目标区域提供足够的浓度，从而提供新型治疗方法。HPP可以通过不同的给药途径给予受试者，例如在高浓度的作用部位局部给药，或者系统给药到生物体内并以更快的速率进入循环系统。