7-nitro-11H-indeno[1,2-b]quinoxalin-11-one | 889950-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-nitro-11H-indeno[1,2-b]quinoxalin-11-one
• 英文别名: 2-nitron-11H-indeno[1,2-b]quinoxalin-11-one；7-Nitroindeno[1,2-b]quinoxalin-11-one
• CAS: 889950-57-6
• 化学式: C₁₅H₇N₃O₃
• 分子量: 277.239
• InChiKey: AGVJVAXKTHULFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 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：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  吗啉 、 7-nitro-11H-indeno[1,2-b]quinoxalin-11-one 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以40%的产率得到2-nitro-11H-indeno[1,2-b]quinoxalin-11-one
  参考文献：
  名称：

  抗肿瘤剂色氨酸的合成与评价

  摘要：

  在这里，通过色氨酸和仲胺在温和的反应条件下反应快速制备 N-取代的色氨酸类似物，开发了一种有效和方便的方法。通过MTT测定法测试所有化合物在癌细胞系中的抗肿瘤活性。结果表明，其中一些对人肿瘤细胞系 A549、HCT116、MDA-MB-231 表现出抗肿瘤活性，IC 50平均值处于低微摩尔水平。具体而言，化合物3b剂量依赖性地诱导A549细胞中的G2/S细胞周期停滞和细胞凋亡。

  DOI：

  10.1016/j.tet.2021.132454
• 作为产物：
  描述：

  1,2,3-茚满三酮 、 4-硝基邻苯二胺 在 poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.1h， 以94%的产率得到7-nitro-11H-indeno[1,2-b]quinoxalin-11-one
  参考文献：
  名称：

  Synthesis of Bisindolylindeno[1,2-b]quinoxaline and Bisindolylindeno[3,4-b]pyrazine with Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide)

  摘要：

  Poly(N,N-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as novel reagent was synthesized. Bisindolylindeno[1,2-b]quinoxaline and bisindolylindeno[3,4-b]pyrazine derivatives were synthesized in a simple and efficient method from the three-component condensation reaction of indole, indane-1,2,3-trione, and diamine aromatic compounds by PBNS under solvent-free conditions at 80 degrees C in good to excellent yields, short reaction times, and a simple procedure for new derivatives. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications((R)) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.829237

文献信息

• Nanomagnetically modified thioglycolic acid (γ‐Fe₂O₃@SiO₂‐SCH₂CO₂H): Efficient and reusable green catalyst for the one‐pot domino synthesis of spiro[benzo[<i>a</i>]benzo[6,7]chromeno[2,3‐<i>c</i>]phenazine] and benzo[<i>a</i>]benzo[6,7]chromeno[2,3‐<i>c</i>]phenazines
  作者：Sajjad Abbasi Pour、Afshin Yazdani‐Elah‐Abadi、Mojgan Afradi

  DOI：10.1002/aoc.3791

  日期：2017.11

  Superparamagnetic nanoparticles of modified thioglycolic acid (γ‐Fe2O3@SiO2‐SCH2CO2H) represent a new, efficient and green catalyst for the one‐pot synthesis of novel spiro[benzo[a]benzo[6,7]chromeno[2,3‐c]phenazine] derivatives via domino Knoevenagel–Michael–cyclization reaction of 2‐hydroxynaphthalene‐1,4‐dione, benzene‐1,2‐diamines, ninhydrin and isatin. This novel magnetic organocatalyst was easily

  改性巯基乙酸（γ-铁的顺磁纳米颗粒2 ö 3 @SiO 2 -SCH 2 CO 2 2H）代表用于一锅合成新颖螺〔苯并[一种新的，有效的和绿色的催化剂一]苯并[6,7 ] chromeno [2,3‐ c[吩嗪]衍生物通过2-羟基萘-1,4-二酮，苯1,2-二胺，茚三酮和靛红的多米诺Knoevenagel–Michael–环化反应而生成。通过使用外部磁体的磁倾析，可以容易地从反应混合物中分离出这种新型的磁性有机催化剂，并且可以重复使用至少六次而不会显着降低其活性。使用各种技术对催化剂进行了充分表征。该方法也成功地用于合成苯并[ a ]苯并[6,7]色酚[2,3- c ]吩嗪。
• Heterogeneous graphene oxide as recyclable catalyst for azomethine ylide mediated 1,3 dipolar cycloaddition reaction in aqueous medium
  作者：Marri Sameer Reddy、Nandigama Satish Kumar、L. Raju Chowhan

  DOI：10.1039/c8ra06714g

  日期：——

  Graphene oxide (GO) catalysed multi component reaction of azomethine ylide driven 1,3 dipolar cycloaddition reaction in aqueous ethanolic solution is reported for the first time. This strategy has been applied for the synthesis of poly heterocyclic spiro-indenoquinoxaline pyrrolizidines and spiro-oxindoles pyrrolizidines with good to excellent yield along with excellent regio and diastereoselectivity

  首次报道了氧化石墨烯（GO）催化偶氮甲碱叶立德驱动的乙醇水溶液中的1,3偶极环加成反应的多组分反应。该策略已被应用于合成多杂环螺茚并喹喔啉吡咯里西啶和螺羟基吲哚吡咯里西啶，具有良好的产率以及优异的区域和非对映选择性。发现 0.50 wt% 的超低催化剂负载量可有效催化反应。
• Applications of novel composite UiO-66-NH₂/Melamine with phosphorous acid tags as a porous and efficient catalyst for the preparation of novel spiro-oxindoles
  作者：Elham Tavakoli、Hassan Sepehrmansourie、Mahmoud Zarei、Mohammad Ali Zolfigol、Ardeshir Khazaei、Mojtaba Hosseinifard

  DOI：10.1039/d2nj03340b

  日期：——

  In this study, we introduce a novel approach for incorporating phosphorus acid tags into a UiO-66-NH2/Melamine-based metal–organic framework (MOF). The structure and morphology of UiO-66-NH2/Melamine/[N(CH2PO3H2)2]2 as a catalyst were characterized using various techniques. The presented catalyst was used in the synthesis of novel spiro-oxindoles via a condensation reaction of isatin derivatives, acenaphthylene-1

  在本研究中，我们介绍了一种将磷酸标签结合到 UiO-66-NH 2 /三聚氰胺基金属有机框架 (MOF) 中的新方法。使用各种技术表征了作为催化剂的 UiO-66-NH 2 /三聚氰胺/[N(CH 2 PO 3 H 2 ) 2 ] 2的结构和形态。所提出的催化剂用于通过靛红衍生物、苊-1,2-二酮或 11 H-茚并[1,2 - b ]喹喔啉-11-酮、巴比妥酸衍生物的缩合反应合成新型螺羟吲哚类化合物， 5-(1 H-吲哚-3-基)-2 H-pyrazol-3-ylamine 和 3-(1 H -indol-3-yl)-1-phenyl-1 H -pyrazol-5-amine 在绿色和温和条件下。
• Synthesis and evaluation of tryptanthrins as antitumor agents
  作者：Baolong Hou、Ying Zhou、Wenyu Li、Jianli Liu、Cuiling Wang

  DOI：10.1016/j.tet.2021.132454

  日期：2021.10

  the reaction of tryptanthrins and secondary amines under mild reaction conditions. All compounds were tested for their anti-tumor activity in cancer cell lines by MTT assay. The results showed that some of them exhibited anti-tumor activity against human tumor cell lines A549, HCT116, MDA-MB-231 with IC50 mean values at a low micromolar level. In particular, compound 3b induced G2/S cell cycle arrest

  在这里，通过色氨酸和仲胺在温和的反应条件下反应快速制备 N-取代的色氨酸类似物，开发了一种有效和方便的方法。通过MTT测定法测试所有化合物在癌细胞系中的抗肿瘤活性。结果表明，其中一些对人肿瘤细胞系 A549、HCT116、MDA-MB-231 表现出抗肿瘤活性，IC 50平均值处于低微摩尔水平。具体而言，化合物3b剂量依赖性地诱导A549细胞中的G2/S细胞周期停滞和细胞凋亡。
• Synthesis of Bisindolylindeno[1,2-b]quinoxaline and Bisindolylindeno[3,4-b]pyrazine with Poly(<i>N,N</i>′-dibromo-<i>N</i>-ethylnaphthyl-2,7-disulfonamide)
  作者：Ardeshir Khazaei、Abdolhossien Massoudi、Mahdieh Chegeni

  DOI：10.1080/00397911.2013.829237

  日期：2014.3.4

  Poly(N,N-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as novel reagent was synthesized. Bisindolylindeno[1,2-b]quinoxaline and bisindolylindeno[3,4-b]pyrazine derivatives were synthesized in a simple and efficient method from the three-component condensation reaction of indole, indane-1,2,3-trione, and diamine aromatic compounds by PBNS under solvent-free conditions at 80 degrees C in good to excellent yields, short reaction times, and a simple procedure for new derivatives. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications((R)) for the following free supplemental resource(s): Full experimental and spectral details.]