3-Hydroxy-3-(ethoxycarbonyl-diazomethyl)-oxindol | 21267-23-2

• 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: 3-Hydroxy-3-(ethoxycarbonyl-diazomethyl)-oxindol
• 英文别名: ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate；ethyl 2-diazo-2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetate
• CAS: 21267-23-2
• 化学式: C₁₂H₁₁N₃O₄
• 分子量: 261.237
• InChiKey: SVQTWPNEFDDNJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-3-(ethoxycarbonyl-diazomethyl)-oxindol 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2,3-二羟基-喹啉-4-羧酸
  参考文献：
  名称：

  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor

  摘要：

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.

  DOI：

  10.1016/0960-894x(96)00031-5
• 作为产物：
  描述：

  重氮乙酸乙酯 、 靛红 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以91%的产率得到3-Hydroxy-3-(ethoxycarbonyl-diazomethyl)-oxindol
  参考文献：
  名称：

  Dirhodium(II)/DBU 金属-有机体系催化靛红与重氮乙酸乙酯的扩环反应：获得 Viridicatin 生物碱的途径

  摘要：

  我们在此介绍了 NHC-二铑 (II)/DBU 催化的靛红与重氮乙酸乙酯的扩环反应。这种新的一锅法产生了 3-羟基-2(1H)-oxoquinoline-4-carboxylate 核心，区域选择性和良好的产率。DFT 机理研究表明，3-羟基吲哚-重氮中间体和二铑 (II) 络合物之间的金属卡宾形成是反应的限速步骤。合成的 3-羟基-2(1H)-氧喹啉-4-羧酸乙酯核心可以很容易地转化为绿色生物碱，通过微波辅助的 3-羟基-4-Suzuki-Miyaura 交叉偶联，产率高达 80%。溴喹啉-2(1H)-一种与芳基硼酸。

  DOI：

  10.1002/ejoc.201300796

文献信息

• Exploring the Synthetic Versatility of the Lewis Acid Induced Decomposition Reaction of α-Diazo-β-hydroxy Esters. The Case of Ethyl Diazo(3-hydroxy-2-oxo-2,3-dihydro-1<i>H</i>-indol-3-yl)acetate
  作者：Antimo Gioiello、Francesco Venturoni、Maura Marinozzi、Benedetto Natalini、Roberto Pellicciari

  DOI：10.1021/jo201205u

  日期：2011.9.16

  Ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate was prepared by aldol-type condensation of ethyl diazoacetate with isatin. A systematic and mechanistic study on the Lewis acid induced decomposition reaction of this valuable diazo precursor was carried out with the aim to gain new insights into the mechanistic aspects of the reaction as well as to further understand the factors and experimental conditions which affect the relative product distribution. The reaction, which may proceed via cationic and noncationic mechanisms, was found to be significantly influenced by the reaction environment determined by the characteristics of the Lewis acid employed, by the ability of the Lewis acid to form a complex with the alcohol functionality of the alpha-diazo-beta-hydroxy ester, and by the polarity and nucleophilicity of the solvent used.
• Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity
  作者：Virginie Suchaud、Fabrice Bailly、Cédric Lion、Enzo Tramontano、Francesca Esposito、Angela Corona、Frauke Christ、Zeger Debyser、Philippe Cotelle

  DOI：10.1016/j.bmcl.2012.04.096

  日期：2012.6

  We report herein the synthesis of a series of 3-hydroxyquinolin-2(1H)-one derivatives. Esters and amide groups were introduced at position 4 of the basis scaffold and some modulations of the benzenic moiety were performed. Most compounds presented selective inhibitory properties in the 10-20 mu M range against HIV-1 reverse transcriptase associated ribonuclease H activity, without affecting the integrase and reverse transcriptase DNA polymerase activities. Unfortunately all tested compounds exhibited high cellular cytotoxicity in cell culture which limited their applications as antiviral agents. (C) 2012 Elsevier Ltd. All rights reserved.