2,3-二甲氧基-6-硝基喹喔啉 | 103273-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2,3-二甲氧基-6-硝基喹喔啉
• 英文名称: 2,3-dimethoxy-6-nitroquinoxaline
• 英文别名: 2,3-Dimethoxy-6-nitro-chinoxalin
• CAS: 103273-90-1
• 化学式: C₁₀H₉N₃O₄
• 分子量: 235.199
• InChiKey: BLDDKVRLYRDZGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-二甲氧基-6-硝基喹喔啉 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以73%的产率得到6-amino-2,3-dimethoxyquinoxaline
  参考文献：
  名称：

  Synthesis of 2,3-Disubstituted 6-Aminoquinoxalines and Their Application to New Fluorescence Derivatization Reagents for Carboxylic Acids

  摘要：

  通过 2,3-二氯-6-硝基喹喔啉与一些亲核物反应，然后催化硝基氢化，合成了荧光 2,3-二取代 6-氨基喹喔啉。此外，研究还证明其中两种化合物是长链羧酸的新型高灵敏度荧光衍生试剂（1 fmol/1 μl进样量）。

  DOI：

  10.1246/cl.1996.369
• 作为产物：
  描述：

  4-硝基邻苯二胺 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 30.5h， 生成 2,3-二甲氧基-6-硝基喹喔啉
  参考文献：
  名称：

  Quinoxalinylurea derivatives as a novel class of JSP-1 inhibitors

  摘要：

  A series of quinoxalinylurea-based inhibitors are synthesized and shown to be the novel and potent inhibitors against Jnk Stimulatory Phosphatase-1 (JSP-1), which is a special member of dual-specificity protein phosphatase (DSP) family. Biological assay and computational modeling studies showed the compounds were reversible and noncompetitive inhibitors of JSP-1. JSP-1 inhibitors may be useful for the treatment of inflammatory, vascular, neurodegenerative, metabolic, and oncological diseases in humans associated with dysfunctional Jnk signaling. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.094

文献信息

• Preparation containing quinoxaline derivatives
  申请人：——

  公开号：US20030207886A1

  公开（公告）日：2003-11-06

  The invention relates to the use of quinoxaline derivatives as photostable UV filters in cosmetic and pharmaceutical preparations for protecting the human epidermis or human hair against UV radiation, especially in the 280-400 nm range.

  该发明涉及在化妆品和药物制剂中使用喹喔啉衍生物作为光稳定的紫外线过滤剂，用于保护人类表皮或人类头发免受紫外线辐射的影响，特别是在280-400纳米范围内。
• Synthesis of 2,3-Disubstituted 6-Aminoquinoxalines and Their Application to New Fluorescence Derivatization Reagents for Carboxylic Acids
  作者：Akira Katoh、Motoki Takahashi、Junko Ohkanda

  DOI：10.1246/cl.1996.369

  日期：1996.5

  Fluorescent 2,3-disubstituted 6-aminoquinoxalines were synthesized by reaction of 2,3-dichloro-6-nitroquinoxaline with some nucleophiles and subsequent catalytic hydrogenation of the nitro group. Further, two of them were demonstrated to be new high-sensitive fluorescence derivatization reagents (1 fmol/1 μl injection volume) for long-chain carboxylic acids.

  通过 2,3-二氯-6-硝基喹喔啉与一些亲核物反应，然后催化硝基氢化，合成了荧光 2,3-二取代 6-氨基喹喔啉。此外，研究还证明其中两种化合物是长链羧酸的新型高灵敏度荧光衍生试剂（1 fmol/1 μl进样量）。
• Quinoxalinylurea derivatives as a novel class of JSP-1 inhibitors
  作者：Li Zhang、Beiying Qiu、Bing Xiong、Xin Li、Jingya Li、Xin Wang、Jia Li、Jingkang Shen

  DOI：10.1016/j.bmcl.2007.01.094

  日期：2007.4

  A series of quinoxalinylurea-based inhibitors are synthesized and shown to be the novel and potent inhibitors against Jnk Stimulatory Phosphatase-1 (JSP-1), which is a special member of dual-specificity protein phosphatase (DSP) family. Biological assay and computational modeling studies showed the compounds were reversible and noncompetitive inhibitors of JSP-1. JSP-1 inhibitors may be useful for the treatment of inflammatory, vascular, neurodegenerative, metabolic, and oncological diseases in humans associated with dysfunctional Jnk signaling. (c) 2007 Elsevier Ltd. All rights reserved.
• New Quinoxaline Derivatives as Potential MT1 and MT2 Receptor Ligands
  作者：Saioa Ancizu、Nerea Castrillo、Silvia Pérez-Silanes、Ignacio Aldana、Antonio Monge、Philippe Delagrange、Daniel-Henry Caignard、Silvia Galiano

  DOI：10.3390/molecules17077737

  日期：——

  Ever since the idea arose that melatonin might promote sleep and resynchronize circadian rhythms, many research groups have centered their efforts on obtaining new melatonin receptor ligands whose pharmacophores include an aliphatic chain of variable length united to an N-alkylamide and a methoxy group (or a bioisostere), linked to a central ring. Substitution of the indole ring found in melatonin with a naphthalene or quinoline ring leads to compounds of similar affinity. The next step in this structural approximation is to introduce a quinoxaline ring (a bioisostere of the quinoline and naphthalene rings) as the central nucleus of future melatoninergic ligands.

  自从有人提出褪黑素可能促进睡眠并重新同步昼夜节律以来，许多研究团队一直致力于获得新的褪黑素受体配体，其药效基团包括一条可变长度的脂肪链，与N-烷基酰胺和一个甲氧基团（或生物等排体）相连，连接在一个中心环上。将褪黑素中的吲哚环替换为萘环或喹啉环会得到亲和力相似的化合物。下一步，在这种结构逼近中，将引入一个喹喔啉环（喹啉环和萘环的生物等排体）作为未来褪黑素能配体的中心核。