4-phenylindoline-2,3-dione | 109082-14-6

• 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: 4-phenylindoline-2,3-dione
• 英文别名: 4-phenyl-1H-indole-2,3-dione
• CAS: 109082-14-6
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: YGNLHANGSLUOIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenylindoline-2,3-dione 在 sodium hydroxide 、 双氧水 作用下， 反应 0.5h， 以13%的产率得到6-phenylanthranilic acid
  参考文献：
  名称：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction from iodoisatins

  摘要：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction with iodoisatins as key intermediates is described. A 'one pot' procedure is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.022
• 作为产物：
  描述：

  3-iodo-isonitrosoacetanilide 在 四(三苯基膦)钯 、 硫酸 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 生成 4-phenylindoline-2,3-dione
  参考文献：
  名称：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction from iodoisatins

  摘要：

  Direct synthesis of new arylanthranilic acids via a Suzuki cross-coupling reaction with iodoisatins as key intermediates is described. A 'one pot' procedure is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.022

文献信息

• Synthesis and Biological Evaluation of Quinoline Salicylic Acids As P-Selectin Antagonists
  作者：Neelu Kaila、Kristin Janz、Silvano DeBernardo、Patricia W. Bedard、Raymond T. Camphausen、Steve Tam、Desirée H. H. Tsao、James C. Keith、Cheryl Nickerson-Nutter、Adam Shilling、Ruth Young-Sciame、Qin Wang

  DOI：10.1021/jm0602256

  日期：2007.1.1

  junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis

  白细胞炎症和组织损伤部位的募集涉及白细胞沿内皮壁滚动，然后白细胞牢固粘附，最后白细胞跨细胞连接转运到下面的组织中。初始滚动步骤由包含活性部分的白细胞糖蛋白（如唾液酸化的Lewisx（sLex））与在内皮细胞上表达的P-选择蛋白的相互作用介导。因此，借助于小分子P-选择蛋白拮抗剂抑制这种相互作用是治疗炎性疾病如关节炎的有吸引力的策略。惠氏化学文库的高通量筛选确定了喹啉水杨酸类化合物（1）作为P-选择素的拮抗剂，其体外和基于细胞的测定方法的功效远远优于sLex。通过迭代药物化学，我们鉴定出具有改善的P-选择素活性，减少的二氢Orate脱氢酶抑制作用和可接受的CYP谱的类似物。铅化合物36在类风湿关节炎的大鼠AIA模型中有效。
• ISATIN AND OXINDOLE COMPOUNDS
  申请人：Kester Robert Francis

  公开号：US20120142705A1

  公开（公告）日：2012-06-07

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.

  本文提供的是公式（I）的化合物及其药用盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗代谢性疾病和紊乱，例如2型糖尿病等，具有用处。
• Decarboxylative Organocatalyzed Addition Reactions of Fluoroacetate Surrogates for the Synthesis of Fluorinated Oxindoles
  作者：Dominik Zetschok、Lukas Heieck、Helma Wennemers

  DOI：10.1021/acs.orglett.1c00172

  日期：2021.3.5

  Fluorinated malonic acid half thioesters (F-MAHTs) were used as thioester enolate equivalents in organocatalyzed addition reactions to isatins. The products from a range of different N-protected and nonprotected isatins were obtained under mild reaction conditions in high yields and enantioselectivities. The unique reactivity of the thioester moiety enabled diverse derivatization and allowed for the

  氟化的丙二酸半硫酯（F-MAHTs）被用作芥子素的有机催化加成反应中的硫酯烯醇盐等效物。在温和的反应条件下，以高收率和对映选择性获得了一系列不同的N-保护的和非保护的靛红的产物。硫酯部分的独特反应性使多种衍生化成为可能，并允许直接获得抗癌药（S）-YK-4-279的氟化类似物（一种抗尤文氏肉瘤的治疗活性化合物）。
• Effect of Structure on Charge Distribution in the Isatin Anions in Aprotic Environment: Spectral Study
  作者：Pavol Tisovský、Róbert Šandrik、Miroslav Horváth、Jana Donovalová、Klaudia Jakusová、Marek Cigáň、Róbert Sokolík、Anton Gáplovský、Martin Gáplovský、Juraj Filo

  DOI：10.3390/molecules22111961

  日期：——

  isatin derivatives. The anions were characterized by ultraviolet–visible (UV–Vis), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy. Interestingly, the anions form aggregates at concentrations above 10−3 mol·dm−3. Further, the effect of cations on the UV–Vis spectra of the studied anions was studied. Charge transfer and its distribution in the anion depends on the radius

  通过使用碱性氟化物和乙酸根阴离子（F- 和 CH3COO-）在非质子溶剂中对初始靛红进行去质子化，制备了五种靛红阴离子。F- 碱度足以使所有研究化合物中的靛红氨氢去质子化。这个过程是可逆的。在质子供体溶剂存在下，阴离子形成相应的靛红。靛红氢酸度取决于靛红衍生物的整体结构。阴离子通过紫外-可见光 (UV-Vis)、傅里叶变换红外 (FTIR) 和核磁共振 (NMR) 光谱进行表征。有趣的是，阴离子在浓度高于 10-3 mol·dm-3 时形成聚集体。此外，研究了阳离子对所研究阴离子的 UV-Vis 光谱的影响。电荷转移及其在阴离子中的分布取决于半径和阳离子电子构型。碱金属阳离子、四丁基铵 (TBA+)、Mg2+ 和 Ag+ 与靛红阴离子的 C-2 羰基氧相互作用。相互作用具有库仑特性。另一方面，Cd2+、Zn2+、Hg2+、Co2+ 和Cu+ 阳离子与靛红氮形成配位键。
• Catalytic Cascade: Efficient Synthesis of Cyclohepta[b]indoles and Cyclohepta[b]indole‐Indoline Conjugates via RCM, Hydrogenation, and Acid‐Catalyzed Ring Expansion
  作者：Nabin Parui、Tirtha Mandal、Sandip Maiti、Jyotirmayee Dash

  DOI：10.1002/chem.202401059

  日期：——

  Efficient catalytic assembly for cyclohepta[b]indoles is achieved through sequential transformations: ring-closing metathesis, catalytic hydrogenation, and acid-catalyzed ring expansion. Ring closing metathesis (RCM) and hydrogenation of oxindoles yield spirocyclohexane-3-oxindoles. A subsequent spontaneous ring expansion-aromatization sequence, catalyzed by either Lewis or Brønsted acid, results in

  环庚[b]吲哚的有效催化组装是通过顺序转化实现的：闭环复分解、催化氢化和酸催化扩环。羟吲哚的闭环复分解（RCM）和氢化产生螺环己烷-3-羟吲哚。随后由路易斯或布朗斯台德酸催化的自发扩环芳构化序列产生环庚[ b ]吲哚或环庚[ b ]吲哚-二氢吲哚缀合物。