3-[4-(dimethylamino)phenyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one | 1491155-28-2

• 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-[4-(dimethylamino)phenyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-[4-(dimethylamino)phenyl]-3-hydroxyindol-2-one；3-[4-(Dimethylamino)phenyl]-3-hydroxy-indol-2-one；3-[4-(dimethylamino)phenyl]-3-hydroxy-1H-indol-2-one
• CAS: 1491155-28-2
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: YMBTXRKYKDGGFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[4-(dimethylamino)phenyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one 在 盐酸 、 乙基溴化镁 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 7.5h， 生成
  参考文献：
  名称：

  具有四碳氨基侧链的光学活性 3,3-二取代羟吲哚衍生物的 COAP/Pd 催化线性不对称烯丙基烷基化

  摘要：

  通过在甲醇中使用手性草酰胺-膦 (COAP-Bn-OMe- p )/钯络合物，开发了乙烯基氮丙啶与 3-芳基羟吲哚的不对称线性选择性烯丙基烷基化反应，可提供多种 3,3-二取代羟吲哚具有良好区域选择性和对映选择性的高收率衍生物。

  DOI：

  10.1021/acs.orglett.2c03902
• 作为产物：
  描述：

  靛红 、 4-(N,N-二甲基)苯胺溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到3-[4-(dimethylamino)phenyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  [EN] 3-3-DI-SUBSTITUTED-OXINDOLES AS INHIBITORS OF TRANSLATION INITIATION
  [FR] OXINDOLES 3,3-DI-SUBSTITUÉS EN TANT QU'INHIBITEURS DE L'INITIATION DE LA TRADUCTION

  摘要：

  提供了用于抑制翻译的组合物和方法。描述了使用二苯氧吲哚化合物治疗（1）细胞增殖性疾病，（2）非增殖性退行性疾病，（3）病毒感染和/或（4）与病毒感染相关的疾病的组合物、方法和试剂盒。

  公开号：

  WO2014047437A1

文献信息

• 3-3-Di-Substituted-Oxindoles as Inhibitors of Translation Initiation
  申请人：President and Fellows of Harvard College

  公开号：US20160106711A1

  公开（公告）日：2016-04-21

  Compositions and methods for inhibiting translation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using diaryloxindole compounds are described.

  本发明提供了用于抑制翻译的组合物和方法。本发明还提供了使用二苯并呋喃衍生物治疗（1）细胞增殖性疾病，（2）非增殖性退行性疾病，（3）病毒感染和/或（4）与病毒感染相关的疾病的组合物、方法和试剂盒。
• Synthesis of Sulfur-Containing Oxindoles by Photoinduced Alkene Difunctionalization via Sulfur 1,2-Relocation
  作者：Cong Lu、Rui Chen、Rui Wang、Dong Jing、Ke Zheng

  DOI：10.1021/acs.orglett.2c04189

  日期：2023.2.10

  which have been widely applied in agrochemicals and pharmaceuticals. Herein, a new approach for the efficient construction of sulfur-containing oxindoles by photoinduced alkene difunctionalization via sulfur 1,2-relocation is developed. The method exhibited a high functional group tolerance and broad substrate compatibility. A library of sulfur-containing oxindole derivatives were synthesized under mild

  有机硫化合物广泛存在于各种天然产物中，广泛应用于农药和医药领域。在此，开发了一种通过硫 1,2-重定位光诱导烯烃双官能化有效构建含硫羟吲哚的新方法。该方法表现出高官能团耐受性和广泛的底物相容性。在温和条件下（无金属、无光催化剂和无添加剂）合成了一个含硫羟吲哚衍生物库。机理研究表明，这种光化学过程是由羟吲哚烯醇化物与氧化还原活性酯形成 EDA 复合物引发的，β-硫基自由基的 C-S 键裂解原位生成烯烃是该过程的关键步骤转型。
• Synthesis and SAR study of novel 3,3-diphenyl-1,3-dihydroindol-2-one derivatives as potent eIF2·GTP·Met-tRNAiMet ternary complex inhibitors
  作者：Séverine Denoyelle、Ting Chen、Hongwei Yang、Limo Chen、Yingzhen Zhang、José A. Halperin、Bertal H. Aktas、Michael Chorev

  DOI：10.1016/j.ejmech.2013.08.030

  日期：2013.11

  The growing recognition of inhibition of translation initiation as a new and promising paradigm for mechanism-based anti-cancer therapeutics is driving the development of potent, specific, and druggable inhibitors. The 3,3-diaryloxindoles were recently reported as potential inhibitors of the elF2.GTP.MettRNAlviet ternary complex assembly and 345-tert-butyl-2-hydroxypheny1}-3-phenyl-1,3-dihydro-2Hindol-2-one #1181 was identified as the prototypic agent of this chemotype. Herein, we report our continuous effort to further develop this chemotype by exploring the structural latitude toward different polar and hydrophobic substitutions. Many of the novel compounds are more potent than the parent compound in the dual luciferase ternary complex reporter assay, activate downstream effectors of reduced ternary complex abundance, and inhibit cancer cell proliferation in the low uM range. Moreover, some of these compounds are decorated with substituents that are known to endow favorable physicochemical properties and as such are good candidates for evaluation in animal models of human cancer. (C) 2013 Elsevier Masson SAS. All rights reserved.
• [EN] 3-3-DI-SUBSTITUTED-OXINDOLES AS INHIBITORS OF TRANSLATION INITIATION<br/>[FR] OXINDOLES 3,3-DI-SUBSTITUÉS EN TANT QU'INHIBITEURS DE L'INITIATION DE LA TRADUCTION
  申请人：HARVARD COLLEGE

  公开号：WO2014047437A1

  公开（公告）日：2014-03-27

  Compositions and methods for inhibiting translation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using diaryloxindole compounds are described.

  提供了用于抑制翻译的组合物和方法。描述了使用二苯氧吲哚化合物治疗（1）细胞增殖性疾病，（2）非增殖性退行性疾病，（3）病毒感染和/或（4）与病毒感染相关的疾病的组合物、方法和试剂盒。
• COAP/Pd-Catalyzed Linear Asymmetric Allylic Alkylation for Optically Active 3,3-Disubstituted Oxindole Derivatives with a Four-Carbon Amino Side Chain
  作者：Wen-Kai Liu、Bai-Lin Wang、Sheng-Suo Zhou、Jun-Hao Shen、Zheng Wang、Xing-Wang Wang

  DOI：10.1021/acs.orglett.2c03902

  日期：2023.1.13

  An asymmetric linear selective allylic alkylation of vinylaziridines with 3-aryl oxindoles has been developed by using a chiral oxamide-phosphine (COAP-Bn-OMe-p)/palladium complex in methanol, which furnished a wide variety of 3,3-disubstituted oxindole derivatives in good yields with excellent regio- and enantioselectivities.

  通过在甲醇中使用手性草酰胺-膦 (COAP-Bn-OMe- p )/钯络合物，开发了乙烯基氮丙啶与 3-芳基羟吲哚的不对称线性选择性烯丙基烷基化反应，可提供多种 3,3-二取代羟吲哚具有良好区域选择性和对映选择性的高收率衍生物。