ethyl 5-hydroxy-2-phenylindole-3-carboxylate | 3189-40-0

• 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: ethyl 5-hydroxy-2-phenylindole-3-carboxylate
• 英文别名: ethyl 5-hydroxy-2-phenyl-1H-indole-3-carboxylate；N-ethyl-5-hydroxyl-2-phenyl-1H-indole-3-ylcarboxylic acid；2-Phenyl-3-carbethoxy-5-hydroxyindol；5-hydroxy-2-phenyl-indole-3-carboxylic acid ethyl ester
• CAS: 3189-40-0
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: LJJGRVZPZCEJHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-2-phenylindole-3-carboxylate 、 碘甲烷 在 氢氧化钾 作用下， 生成 ethyl 5-methoxy-1-methyl-2-phenyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Indolequinone Antitumor Agents:  Correlation between Quinone Structure, Rate of Metabolism by Recombinant Human NAD(P)H:Quinone Oxidoreductase, and in Vitro Cytotoxicity

  摘要：

  A series of indolequinones bearing various functional groups has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H: quinone oxidoreductase (NQO1) were studied. Thus 5-methoxyindolequinones were prepared by the Nenitzescu reaction, followed by functional group interconversions. The methoxy group was subsequently displaced by amine nucleophiles to give a series of amine-substituted quinones. Metabolism of the quinones by NQO1 revealed that, in general, compounds with electron-withdrawing groups at the indole 3-position were among the best substrates, whereas those with amine groups at the 5-position were poor substrates. Compounds with a leaving group at the 3-indolyl methyl position generally inactivated the enzyme. The toxicity toward non-small-cell lung cancer cells with either high NQO1 activity (H460) or no detectable activity (H596) was also studied in representative quinones. Compounds which were good substrates for NQO1 showed the highest selectivity between the two cell lines.

  DOI：

  10.1021/jm980328r
• 作为产物：
  描述：

  在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以69%的产率得到ethyl 5-hydroxy-2-phenylindole-3-carboxylate
  参考文献：
  名称：

  有氧条件下可见光促进单一光敏剂合成吲哚

  摘要：

  取代的吲哚骨架的结构始终是合成化学家关注的重要问题，因为其天然结构存在于天然产物和生物分子中。在这里，我们仅通过在空气气氛下在DMSO溶液中催化量的铱（III）光敏剂（PS）进行自由基环化就可以成功地从多种简单的烯胺中制备吲哚及其衍生物。机理研究表明，该反应涉及自由基过程，以在可见光照射下完成烯胺向吲哚的转化。

  DOI：

  10.1021/acs.orglett.7b01367

文献信息

• Tandem Blaise–Nenitzescu reaction: one-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles
  作者：Yu Sung Chun、Ka Yeon Ryu、Ju Hyun Kim、Hyunik Shin、Sang-gi Lee

  DOI：10.1039/c0ob01024c

  日期：——

  In contrast to the reaction of benzoquinones with β-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of β-enaminoesters, with benzoquinone affords 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise–Nenitzescu reaction).

  与苯醌和β-烯胺酯反应生成吲哚（Nenitzescu反应）不同，Blaise反应中间体，即β-烯胺酯的锌溴络合物与苯醌进行一锅法串联反应，可以高至极佳产率地得到5-羟基-α-(氨基亚甲基)苯并呋喃-2(3H)-酮（Blaise-Nenitzescu串联反应）。
• 一类苯并呋喃及苯并呋喃香豆素衍生物及其制备方法和应用
  申请人：华东师范大学

  公开号：CN109942523B

  公开（公告）日：2023-06-09

  本发明公开了如式(I)、(II)、(III)、(IV)所示的苯并呋喃类及Coumestans衍生物及其制备方法，以及所述苯并呋喃类及Coumestans衍生物化合物在治疗耐多药性肺结核疾病中的应用。本发明所述苯并呋喃类及Coumestans衍生物是一类结构新颖，抑菌效果显著的抗结核杆菌化合物，它是以结核杆菌pks13基因片段编码的聚酮合酶为作用靶点，抑制微生物的生长繁殖，尤其是抑制结核分枝杆菌细胞壁中分枝菌酸的合成，在医药领域具有潜在的应用前景。
• Lewis acid catalyzed nenitzescu indole synthesis
  作者：Valeriya S. Velezheva、Albert G. Kornienko、Sergey V. Topilin、Ascar D. Turashev、Alexander S. Peregudov、Patrick J. Brennan

  DOI：10.1002/jhet.5570430410

  日期：2006.7

  A novel method for Lewis acid catalyzed Nenitzescu indole syntheses of 5-hydroxyindoles bearing different substituents in positions 1 )Alk, Bn, Ar), 2 )Me, Et, Ph), and 3 )COOEt, COMe, CONHPh) as well as tricyclic derivatives are reported. The method is simple, rapid, efficient, and allows preparation of hydroxyindoles from 1,4-benzoquinone and enamines in good to excellent yields with the use of low-polar

  Lewis酸催化Nenitzescu吲哚合成5羟基吲哚的新方法，该位置在1）Alk，Bn，Ar），2）Me，Et，Ph）和3）COOEt，COMe，CONHPh）和三环上带有不同的取代基报告了衍生物。该方法简单，快速，有效，并且在弱路易斯酸催化剂的存在下，使用低极性溶剂，可以由1,4-苯醌和烯胺制备羟基吲哚，产率高至优异。用非氧化还原机理解释了在这种温和条件下5-羟基吲哚的形成。
• Indolequinone Antitumor Agents:  Correlation between Quinone Structure, Rate of Metabolism by Recombinant Human NAD(P)H:Quinone Oxidoreductase, and in Vitro Cytotoxicity
  作者：Howard D. Beall、Shannon Winski、Elizabeth Swann、Anna R. Hudnott、Ann S. Cotterill、Noeleen O'Sullivan、Stephen J. Green、Richard Bien、David Siegel、David Ross、Christopher J. Moody

  DOI：10.1021/jm980328r

  日期：1998.11.1

  A series of indolequinones bearing various functional groups has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H: quinone oxidoreductase (NQO1) were studied. Thus 5-methoxyindolequinones were prepared by the Nenitzescu reaction, followed by functional group interconversions. The methoxy group was subsequently displaced by amine nucleophiles to give a series of amine-substituted quinones. Metabolism of the quinones by NQO1 revealed that, in general, compounds with electron-withdrawing groups at the indole 3-position were among the best substrates, whereas those with amine groups at the 5-position were poor substrates. Compounds with a leaving group at the 3-indolyl methyl position generally inactivated the enzyme. The toxicity toward non-small-cell lung cancer cells with either high NQO1 activity (H460) or no detectable activity (H596) was also studied in representative quinones. Compounds which were good substrates for NQO1 showed the highest selectivity between the two cell lines.
• Visible Light Promoted Synthesis of Indoles by Single Photosensitizer under Aerobic Conditions
  作者：Wen-Qiang Liu、Tao Lei、Zi-Qi Song、Xiu-Long Yang、Cheng-Juan Wu、Xin Jiang、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.orglett.7b01367

  日期：2017.6.16

  The construction of substituted indole skeletons is always an important concern of synthetic chemists because of its prevalent structure found in natural products and biological molecules. Here, we succeeded in preparing indoles and their derivatives from a wide variety of simple enamines via radical cyclization only with catalytic amounts of an iridium(III) photosensitizer (PS) in DMSO solution under

  取代的吲哚骨架的结构始终是合成化学家关注的重要问题，因为其天然结构存在于天然产物和生物分子中。在这里，我们仅通过在空气气氛下在DMSO溶液中催化量的铱（III）光敏剂（PS）进行自由基环化就可以成功地从多种简单的烯胺中制备吲哚及其衍生物。机理研究表明，该反应涉及自由基过程，以在可见光照射下完成烯胺向吲哚的转化。