Isopropyl-(3-nitro-quinolin-4-yl)-amine | 39558-79-7

• 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: Isopropyl-(3-nitro-quinolin-4-yl)-amine
• 英文别名: 3-Nitro-N-(propan-2-yl)quinolin-4-amine；3-nitro-N-propan-2-ylquinolin-4-amine
• CAS: 39558-79-7
• 化学式: C₁₂H₁₃N₃O₂
• mdl: MFCD21496428
• 分子量: 231.254
• InChiKey: QJTAAAIBXPZNIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Isopropyl-(3-nitro-quinolin-4-yl)-amine 在 platinum on activated charcoal 过氧乙酸 、 氨 、 氢气 、 magnesium sulfate 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 60.0~150.0 ℃ 、344.74 kPa 条件下， 生成 1-Isopropyl-1H-imidazo[4,5-c]quinolin-4-ylamine
  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-羟基喹啉 在 草酰氯 、 硝酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Isopropyl-(3-nitro-quinolin-4-yl)-amine
  参考文献：
  名称：

  基于TLR7的化合物对化学疗法引起的脱发的设计，合成和生物学活性。

  摘要：

  脱发是癌症化学疗法中常见的皮肤病症状和副作用。咪喹莫特在中期和晚期的telogen的应用激活了毛囊干细胞，导致过早进入毛发周期。基于喹啉结构，新合成的化合物6b通过支链置换和三唑环环化在体内和体外显示出增殖活性。Toll样受体（TLR）也是免疫系统的关键介体，其激活与各种疾病有关。本研究旨在在TLR7（PDB代码：5GMH）的共结晶内扩展新的激动剂。然而，对NF-κB活性和NO抑制的生物学分析表明，所选的5种化合物是TLR7拮抗剂。分子对接表明结合方式的差异：

  DOI：

  10.1007/s10637-019-00793-5

文献信息

• Continuous-Flow Synthesis of 1<i>-</i>Substituted Benzotriazoles from Chloronitrobenzenes and Amines in a CN Bond Formation/Hydrogenation/Diazotization/Cyclization Sequence
  作者：Mao Chen、Stephen L. Buchwald

  DOI：10.1002/anie.201300615

  日期：2013.4.8

  Two approaches have been developed for the regiospecific continuous‐flow synthesis of 1‐substituted benzotriazoles. They begin with either an SNAr reaction at high temperature or Pd catalysis and involve consecutive multiphase processes, allowing the multistep synthesis of benzotriazoles to take place in an efficient manner (see picture).

  已经开发出两种方法用于1-取代的苯并三唑的区域特异性连续流动合成。它们从高温下的S N Ar反应或Pd催化开始，并且涉及连续的多相过程，从而可以高效地进行苯并三唑的多步合成（见图）。
• Synthesis and Structure−Activity-Relationships of 1<i>H</i>-Imidazo[4,5-<i>c</i>]quinolines That Induce Interferon Production
  作者：John F. Gerster、Kyle J. Lindstrom、Richard L. Miller、Mark A. Tomai、Woubalem Birmachu、Shannon N. Bomersine、Shiela J. Gibson、Linda M. Imbertson、Joel R. Jacobson、Roy T. Knafla、Peter V. Maye、Nickolas Nikolaides、Folakemi Y. Oneyemi、Gwen J. Parkhurst、Sharon E. Pecore、Michael J. Reiter、Lisa S. Scribner、Tracy L. Testerman、Natalie J. Thompson、Tammy L. Wagner、Charles E. Weeks、Jean-Denis Andre、Daniel Lagain、Yvon Bastard、Michel Lupu

  DOI：10.1021/jm049211v

  日期：2005.5.1

  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.
• Design, synthesis, and biological activity of TLR7-based compounds for chemotherapy-induced alopecia
  作者：Jincheng Yang、Kun Chen、Bin Wang、Liudi Wang、Shuya Qi、Weihua Wang

  DOI：10.1007/s10637-019-00793-5

  日期：2020.2

  synthesized compound 6b displayed proliferation activity in vitro and in vivo through branch chain replacement and triazole ring cyclization. Toll-like receptors (TLRs) are also critical mediators of the immune system, and their activation is linked to various diseases. The present study aimed to expand new agonists within co-crystallization of TLR7 (PDB code: 5GMH); however, biological assays of NF-κB

  脱发是癌症化学疗法中常见的皮肤病症状和副作用。咪喹莫特在中期和晚期的telogen的应用激活了毛囊干细胞，导致过早进入毛发周期。基于喹啉结构，新合成的化合物6b通过支链置换和三唑环环化在体内和体外显示出增殖活性。Toll样受体（TLR）也是免疫系统的关键介体，其激活与各种疾病有关。本研究旨在在TLR7（PDB代码：5GMH）的共结晶内扩展新的激动剂。然而，对NF-κB活性和NO抑制的生物学分析表明，所选的5种化合物是TLR7拮抗剂。分子对接表明结合方式的差异：