6H-吲哚并[2,3-b]喹喔啉 | 243-59-4

• 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: 6H-吲哚并[2,3-b]喹喔啉
• 英文名称: indophenazine
• 英文别名: 6H-indolo[2,3-b]quinoxaline；indolo<2,3-b>quinoxaline；6H-Indolo<2,3-b>chinoxalin；Indolo<2,3-b>chinoxalin；6H-indolo [3,2-b]quinoxaline；6H-indolo[3,2-b]quinoxaline
• CAS: 243-59-4
• 化学式: C₁₄H₉N₃
• mdl: MFCD00068754
• 分子量: 219.246
• InChiKey: LCKIWLDOHFUYDV-UHFFFAOYSA-N

物化性质

• 沸点：
  430.5±28.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 熔点：
  295-297 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6H-吲哚并[2,3-b]喹喔啉 在 N-溴代丁二酰亚胺(NBS) 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 9-bromo-6-butyl-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  Synthesis, Spectra, and Theoretical Investigations of the Triarylamines Based on 6H-Indolo[2,3-b]quinoxaline

  摘要：

  Triarylamines containing a 6H-indolo[2,3-b]quinoxaline core and aromatic units such as phenyl, naphthyl, pyrene, anthracene, or fluorene have been synthesized by employing palladium-catalyzed C-N and C-C coupling reactions and characterized by optical absorption and emission spectra, electrochemical behavior, and thermal studies. Even though the electronic absorption spectra of the compounds were influenced by the nature of the peripheral amines, the emission spectra indicated close similarity for the excited states in these compounds. For the derivatives in which the amines were directly anchored on the 6H-indolo[2,3-b]quinoxaline nucleus, the emission appeared to be dominated by the state localized on the 6H-indolo[2,3-b]quinoxaline chromophore, while in the compounds containing the extended conjugation the fluorescence originated from the polyaromatic linker. The compounds displayed green or yellow emission depending on the nature of the amine segment. All of the dyes displayed one-electron quasi-reversible oxidation couple in the cyclic voltammograms, which is attributable to the oxidation of the peripheral amines at the 6H-indolo[2,3-b]-quinoxaline core. An additional one-electron oxidation process observable at the high positive potentials for the compounds 7 and 8 probably arises from the oxidation of the arylthiophene segment. The enhanced thermal stability and relatively higher glass transition temperatures observed for these compounds were attributed to the presence of dipolar 6H-indolo[2,3-b]quinox. aline segment. The origin of the optical spectra and the trends observed therein were rationalized using TDDFT simulations.

  DOI：

  10.1021/jo1016663
• 作为产物：
  描述：

  N-乙酰基-3-吲哚啉酮 在 氢氧化钾 、 溴 、 四氯苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 74.33h， 生成 6H-吲哚并[2,3-b]喹喔啉
  参考文献：
  名称：

  A Straightforward Synthesis of Pyridopyrazino[2,3-b]indoles and Indolo[2,3-b]quinoxaline

  摘要：

  DOI：

  10.3987/com-01-9181

文献信息

• One-Pot Construction of Indolo[2,3-<i>b</i>]quinoxalines through Ruthenium-Catalyzed <i>Ortho</i> C–H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides
  作者：Sudip Laru、Suvam Bhattacharjee、Sumit Ghosh、Alakananda Hajra

  DOI：10.1021/acs.orglett.1c02837

  日期：2021.10.1

  N-substituted indolo[2,3-b]quinoxalines has been developed through a Ru(II)-catalyzed ortho C–H functionalization of 2-arylquinoxalines with sulfonyl azides and further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in one pot. This double C–N bond formation strategy provides a new efficient route for the preparation of a series of biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives in

  N-取代的吲哚并[2,3- b ]喹喔啉的合成是通过Ru(II)催化的2-芳基喹喔啉与磺酰叠氮化物的邻位C-H官能化并用2,3-二氯-5进一步氧化而开发的， 6-二氰基-1,4-苯醌一锅。这种双C-N键形成策略为制备一系列生物相关的6 H-吲哚[2,3- b ]喹喔啉衍生物提供了一条新的有效途径，产率高达94%，表明底物适用范围广泛。初步的机理研究表明，连续的 C-N 键形成是通过第一步中五元钌环中间体的形成和第二步中自由基机制的形成进行的。
• Microwave-assisted Synthesis of 6-{(5-Aryl-1,3,4-oxadiazol-2-yl)methyl}-6<i>H</i>-indolo[2,3-<i>b</i>]quinoxalines
  作者：Sreenivas Avula、Jayaram Reddy Komsani、Satish Koppireddi、Rambabu Yadla

  DOI：10.1002/jhet.2272

  日期：2015.11

  convenient synthesis of a new series of 2‐(6H‐indolo[2,3‐b]quinoxalin‐6‐yl)methyl}‐5‐aryl‐1,3,4‐oxadiazoles from readily available 1,2‐diaminobenzene and isatins under microwave irradiation conditions was disclosed. The 6‐(5‐aryl‐1,3,4‐oxadiazol‐2‐yl)methyl}‐6H‐indolo[2,3‐b]quinoxalines were also prepared by the thermal cyclo‐condensation reaction of 2‐(6H‐indolo[2,3‐b]quinoxalin‐6‐yl)acetohydrazides

  从现成的1,2，（6 H-吲哚[2,3 - b ]喹喔啉-6-基）甲基} -5-芳基-1,3,4-恶二唑中高效合成新的系列1，公开了在微波辐射条件下的2-二氨基苯和靛红。6-（5-芳基-1,3,4-恶二唑-2-基）甲基} -6 H-吲哚并[2,3- b ]喹喔啉也可以通过2-（-在回流的POCl 3中将6 H-吲哚并[2,3 - b ]喹喔啉-6-基）乙酰肼与羧酸一起使用。与热反应方案相比，微波辅助合成快速，可在较低的操作温度下提高产品的收率，减少废物的产生。
• Cerium oxide nanoparticle-catalyzed three-component protocol for the synthesis of highly substituted novel quinoxalin-2-amine derivatives and 3,4-dihydroquinoxalin-2-amines in water
  作者：Naushad Edayadulla、Yong Rok Lee

  DOI：10.1039/c4ra00717d

  日期：——

  The syntheses of novel quinoxalin-2-amine derivatives were conducted in water using CeO2 nanoparticle catalyzed three-component reactions of 1,2-diamines with aldehydes and isocyanides. A variety of 3,4-dihydroquinoxalin-2-amine derivatives were also synthesized by reactions between 1,2-diamines, ketones and isocyanides. This new method offers an environmentally benign and effective approach for the

  使用CeO 2纳米颗粒催化1,2-二胺与醛和异氰酸酯的三组分反应，在水中进行了新的喹喔啉-2-胺衍生物的合成。通过1，2-二胺，酮和异氰酸酯之间的反应，还合成了多种3，4-二氢喹喔啉-2-胺衍生物。这种新方法为合成喹喔啉-2-胺和3,4-二氢喹喔啉-2-胺提供了一种对环境无害且有效的方法。
• [EN] METHODS AND COMPOSITIONS OF SUBSTITUTED 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE ANALOGS AS INHIBITORS OF BETA-CATENIN/T-CELL FACTOR PROTEIN-PROTEIN INTERACTIONS<br/>[FR] PROCÉDÉS ET COMPOSITIONS D'ANALOGUES SUBSTITUÉS DE 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE UTILISÉS COMME INHIBITEURS DES INTERACTIONS PROTÉINE-PROTÉINE BÊTA-CATÉNINE/FACTEURS TCF
  申请人：UNIV UTAH RES FOUND

  公开号：WO2016187050A1

  公开（公告）日：2016-11-24

  In one aspect, the invention relates to substituted 5H-[1,2,5]oxadiazolo [3',4':5,6]pyrazino[2,3-b]indole analogues, derivatives thereof, and related compound; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders, e.g., various tumors and cancers, associated with a β-catenin/T-cell factor interaction dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，该发明涉及替代的5H-[1,2,5]噁二唑[3',4':5,6]吡唑并[2,3-b]吲哚类似物，其衍生物以及相关化合物；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与β-连环蛋白/T细胞因子相互作用功能障碍相关的疾病的方法，例如各种肿瘤和癌症。本摘要旨在作为在特定领域搜索的扫描工具，并不旨在限制本发明。
• Virtual screening, synthesis and biological evaluation of DNA intercalating antiviral agents
  作者：Kyrylo Klimenko、Sergey Lyakhov、Marina Shibinskaya、Alexander Karpenko、Gilles Marcou、Dragos Horvath、Marina Zenkova、Elena Goncharova、Rinat Amirkhanov、Andrei Krysko、Sergei Andronati、Igor Levandovskiy、Pavel Polishchuk、Victor Kuz'min、Alexandre Varnek

  DOI：10.1016/j.bmcl.2017.06.035

  日期：2017.8

  scaffolds of known DNA intercalators. This resulted in 12 hits which then were synthesized and tested for antiviral activity against VaV together with 43 compounds earlier studied against VSV. Two compounds displaying high antiviral activity against VaV and low cytotoxicity were selected for further antiviral activity investigations.

  本文介绍了计算机辅助设计的新型抗痘苗病毒（VACV）的抗病毒剂，它们可能充当核酸嵌入剂。较早获得的DNA嵌入亲和力和抗水泡性口炎病毒（VSV）活性的实验数据已分别用于建立药效团和QSAR模型。这些模型用于虚拟筛选在已知DNA嵌入剂的典型支架周围产生的245个分子的数据库。这产生了12个命中，然后合成并测试了针对VaV的抗病毒活性，以及先前研究的针对VSV的43种化合物。选择了两种对VaV具有高抗病毒活性和低细胞毒性的化合物进行进一步的抗病毒活性研究。

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