2-amino-7-nitroquinoline | 49609-04-3

• 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: 2-amino-7-nitroquinoline
• 英文别名: 2-Amino-7-nitroquinolin；7-Nitroquinolin-2-amine
• CAS: 49609-04-3
• 化学式: C₉H₇N₃O₂
• 分子量: 189.173
• InChiKey: STVRCCRLJQADFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-7-nitroquinoline 在 镍 氢气 作用下， 以 丙酮 为溶剂， 生成 喹啉-2,7-二胺
  参考文献：
  名称：

  7-Aminoquinolines. A novel class of agents active against herpes viruses

  摘要：

  A series of 7-aminoquinoline derivatives was synthesized and evaluated for their capacity to produce cytotoxicity in KB cells and to inhibit the replication of herpes simplex virus (HSV) type 1. All compounds tested inhibited the replication of HSV-1 with 50% inhibitory concentrations in the range of 2-50 micrograms/mL. The antiviral activity of many compounds, however, was separated from cytotoxicity to replicating uninfected cells by only two- to fivefold higher than those required for antiviral activity. Nonetheless, six compounds (10, 28, 29, 32, 34, and 36) were identified in which the separation was greater than fivefold. All compounds examined were more potent inhibitors of viral DNA synthesis than the cellular DNA synthesis.

  DOI：

  10.1021/jm00402a016
• 作为产物：
  描述：

  7-硝基喹啉-2-醇 在 氨 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 2-amino-7-nitroquinoline
  参考文献：
  名称：

  7-Aminoquinolines. A novel class of agents active against herpes viruses

  摘要：

  A series of 7-aminoquinoline derivatives was synthesized and evaluated for their capacity to produce cytotoxicity in KB cells and to inhibit the replication of herpes simplex virus (HSV) type 1. All compounds tested inhibited the replication of HSV-1 with 50% inhibitory concentrations in the range of 2-50 micrograms/mL. The antiviral activity of many compounds, however, was separated from cytotoxicity to replicating uninfected cells by only two- to fivefold higher than those required for antiviral activity. Nonetheless, six compounds (10, 28, 29, 32, 34, and 36) were identified in which the separation was greater than fivefold. All compounds examined were more potent inhibitors of viral DNA synthesis than the cellular DNA synthesis.

  DOI：

  10.1021/jm00402a016

文献信息

• The ability of a triplex-forming oligonucleotide to recognize T-A and C-G base pairs in a DNA duplex is enhanced by incorporating N-acetyl-2,7-diaminoquinoline
  作者：Akihiro Ohkubo、Tatsuya Ohnishi、Shuhei Nishizawa、Yuri Nishimura、Shugo Hisamatsu

  DOI：10.1016/j.bmc.2020.115350

  日期：2020.4

  can recognize the homopurine-homopyrimidine sequence in DNA duplexes and inhibit the transcription of targeted mRNAs. Recently, we reported that N-acetyl-2,7-diamino-1,8-naphthyridine (DANac), incorporated into a TFO, has high binding ability and base recognition selectivity for the pyrimidine bases in the purine-rich chain of the DNA duplex at pH 7.4. However, it was found in this study that the difference

  形成三链体的寡核苷酸（TFO）可以识别DNA双链体中的高嘌呤-高嘧啶序列，并抑制目标mRNA的转录。最近，我们报道了掺入TFO中的N-乙酰基2,7-二氨基-1,8-萘啶（DANac）对DNA富嘌呤链中的嘧啶碱基具有很高的结合能力和碱基识别选择性。 pH 7.4的双链体。但是，在这项研究中发现，在pH 6.0-7.0下，嘧啶碱基和嘌呤碱基之间的Tm值差异降低了4°C以上。为了提高TFO的低碱基识别选择性，我们设计了一种具有喹啉骨架的新型人工碱基DAQac。在pH 7.4时，含有DAQac：TA或DAQac：CG的三元组的Tm值比含有DAQac：AT或DAQac：GC的三元组的Tm值高13°C以上。我们还观察到，在更酸性的条件下（pH 6.0-7.0），DAQac在三元组中的碱基识别选择性高于DANac，尽管DAQac在三元组中的结合能力与DANac相似。此外，我们发现，结合到TFO中的DAQ
• NASR, M.;DRACH, J. C.;SMITH, S. H.;SHIPMAN, CH. , (JR);BURCKHALTER, J. H., J. MED. CHEM., 31,(1988) N 7, C. 1347-1351
  作者：NASR, M.、DRACH, J. C.、SMITH, S. H.、SHIPMAN, CH. , (JR)、BURCKHALTER, J. H.

  DOI：——

  日期：——
• [EN] SH3 PROTEIN DOMAINS AND THEIR LIGANDS<br/>[FR] DOMAINES PROTEINIQUES SH3 ET LEURS LIGANDS
  申请人：ADELAIDE RES & INNOVATION PTY

  公开号：WO2003013523A1

  公开（公告）日：2003-02-20

  The present invention relates generally to molecules capable of interaction with one or more domains within a proteinaceous molecule such as a peptide, polypeptide, protein or a macromolecule comprising a proteinaceous molecule. More particularly the present invention relates to molecules including ligands which are capable of interacting with, and more particularly, binding to, SH3 protein domains or homologs thereof and even more particularly to molecules including ligands which are capable of binding to SH3 domains having a three-dimensional ligand-binding site comprising a negatively charged residue and a hydrophobic residue linearly separated by at least five amino acid residues. The subject invention is preferably directed to the use of 2-aminopyridine, 2-aminoquinoline, 1-aminoisoquinoline and derivatives, homologs, analogs and mimetics thereof or pharmaceutically acceptable salts thereof which interact with SH3 domains, and more particularly to the binding of 2-aminopyridine, 2-aminoquinoline, 1-aminoisoquinoline and derivatives analogs and mimetics to SH3 domains as defined above. The present invention contemplates the use of a three dimensional structure of the subject SH3 domain to identify, screen and design amino-substituted and amino-substituted pyridines and aminoquinolines capable of binding to an SH3 domain. The present invention is also useful for the in silico selection of derivatives homologs, analogs and mimetics of 2-aminopyridine, 2-aminoquinoline, 1-aminoisoquinoline capable of binding to SH3 domains. The ligands of the present invention are useful in the development of a range of therapeutic and diagnostic agents.
• 7-Aminoquinolines. A novel class of agents active against herpes viruses
  作者：Mohamed Nasr、John C. Drach、Sandra H. Smith、Charles Shipman、J. H. Burckhalter

  DOI：10.1021/jm00402a016

  日期：1988.7

  A series of 7-aminoquinoline derivatives was synthesized and evaluated for their capacity to produce cytotoxicity in KB cells and to inhibit the replication of herpes simplex virus (HSV) type 1. All compounds tested inhibited the replication of HSV-1 with 50% inhibitory concentrations in the range of 2-50 micrograms/mL. The antiviral activity of many compounds, however, was separated from cytotoxicity to replicating uninfected cells by only two- to fivefold higher than those required for antiviral activity. Nonetheless, six compounds (10, 28, 29, 32, 34, and 36) were identified in which the separation was greater than fivefold. All compounds examined were more potent inhibitors of viral DNA synthesis than the cellular DNA synthesis.