5-methoxy-3-oxo-2-phenyl-3H-indole 1-oxide | 6127-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methoxy-3-oxo-2-phenyl-3H-indole 1-oxide
• 英文别名: 5-Methoxy-1-oxido-2-phenylindol-1-ium-3-one
• CAS: 6127-33-9
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: ZQVBYFDEGOFPGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-oxo-2-phenyl-3H-indole 1-oxide 在 indium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以61%的产率得到5-methoxy-2-phenyl-3H-indol-3-one
  参考文献：
  名称：

  2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities

  摘要：

  The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2(4-dimethylaminophenyl)-5-methoxy-indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.059
• 作为产物：
  描述：

  4-methoxy-1-nitro-2-(phenylethynyl)benzene 在 双(乙腈)氯化钯(II) 作用下， 以 乙腈 为溶剂， 以46 %的产率得到5-methoxy-3-oxo-2-phenyl-3H-indole 1-oxide
  参考文献：
  名称：

  Rh(III)-催化的靛红与丙二酸重氮酯的 C7-烷基化

  摘要：

  已经开发出 Rh(III) 催化的靛红素（二氢吲哚-3-酮N-氧化物）与丙二酸重氮酯的 C7 烷基化反应。该策略利用靛蓝蛋白N-氧化物基团上的氧阴离子作为导向基团，成功合成了一系列C7-烷基化靛蓝蛋白，收率中等至良好（48-86%）。此外，异酪素的N-氧化物不仅可以作为C7-H键断裂的简单导向基团，而且可以脱氧以便于去除。

  DOI：

  10.1021/acs.joc.3c02405

文献信息

• Investigation of a Late-Stage Derivatiza­tion Approach to Isatogens: Discovery of New Reaction Pathways
  作者：Steven J. Edeson、Elvis J. M. Maduli、Stephen Swanson、Panayiotis A. Procopiou、Joseph P. A. Harrity

  DOI：10.1002/ejoc.201501372

  日期：2016.1

  We have developed a new strategy for preparing 2-substituted indolone N-oxides (isatogens) by substitution reactions with aryl- and alkyl-organometallic reagents. This approach allows a range of substituents to be incorporated at a late stage and complements existing methods that necessitate their early stage incorporation during substrate preparation. Further chemistry has been found to take place

  我们开发了一种通过与芳基和烷基有机金属试剂进行取代反应来制备 2-取代吲哚酮 N-氧化物（isatogens）的新策略。这种方法允许在后期阶段引入一系列取代基，并补充了在底物制备过程中需要早期引入的现有方法。已经发现在硝酮部分发生了进一步的化学反应；分子内偶极环加成提供了获得有角度稠合的三环杂环的途径。然而，更不寻常的是，这些化合物易于通过有机锌试剂进一步加成，从而产生 2,2-二取代的 3-羟吲哚产物。
• 2-Iodoisatogens: Versatile Intermediates for the Synthesis of Nitrogen Heterocycles
  作者：Elvis J. M. Maduli、Steven J. Edeson、Stephen Swanson、Panayiotis A. Procopiou、Joseph P. A. Harrity

  DOI：10.1021/ol503487f

  日期：2015.1.16

  A Cu-promoted cyclization of 2-nitrophenyl iodoacetylenes provides a direct route to a range of 2-iodoisatogens. These compounds represent useful intermediates for the late-stage elaboration of the C-I bond to furnish isatins and a range of alternative heterocyclic products.
• 2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
  作者：Ennaji Najahi、Alexis Valentin、Paul-Louis Fabre、Karine Reybier、Françoise Nepveu

  DOI：10.1016/j.ejmech.2014.03.059

  日期：2014.5

  The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2(4-dimethylaminophenyl)-5-methoxy-indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Rh(III)-Catalyzed C7-Alkylation of Isatogens with Malonic Acid Diazoesters
  作者：Xiang Guan、Wen-Jie Li、Ming-Shan Shuai、Mao Zhang、Chao-Chao Zhou、Xiao-Zhong Fu、Yuan-Yong Yang、Meng Zhou、Bin He、Yong-Long Zhao

  DOI：10.1021/acs.joc.3c02405

  日期：2024.3.1

  Rh(III)-catalyzed C7-alkylation of isatogens (indolin-3-one N-oxides) with malonic acid diazoesters has been developed. This strategy utilizes oxygen anion on the N-oxide group of isatogens as a directing group and successfully achieves the synthesis of a series of C7-alkylated isatogens with moderate to good yields (48–86% yields). Moreover, the N-oxides of isatogens can not only serve as the simple

  已经开发出 Rh(III) 催化的靛红素（二氢吲哚-3-酮N-氧化物）与丙二酸重氮酯的 C7 烷基化反应。该策略利用靛蓝蛋白N-氧化物基团上的氧阴离子作为导向基团，成功合成了一系列C7-烷基化靛蓝蛋白，收率中等至良好（48-86%）。此外，异酪素的N-氧化物不仅可以作为C7-H键断裂的简单导向基团，而且可以脱氧以便于去除。