1-(1-benzyl-1H-indol-3-yl)-2-(thiophen-2-yl)ethane-1,2-dione | 1489263-05-9

• 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: 1-(1-benzyl-1H-indol-3-yl)-2-(thiophen-2-yl)ethane-1,2-dione
• 英文别名: 1-(1-Benzylindol-3-yl)-2-thiophen-2-ylethane-1,2-dione；1-(1-benzylindol-3-yl)-2-thiophen-2-ylethane-1,2-dione
• CAS: 1489263-05-9
• 化学式: C₂₁H₁₅NO₂S
• 分子量: 345.422
• InChiKey: QOBRGTDQFMFYEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩乙醛酸 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(1-benzyl-1H-indol-3-yl)-2-(thiophen-2-yl)ethane-1,2-dione
  参考文献：
  名称：

  Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives

  摘要：

  We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A(2B) AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A(2A) and A(3) ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A(1) AR. When tested on A(2B) AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A(2B) AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.001

文献信息

• KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles
  作者：Bochao Zhou、Shiyu Guo、Zheng Fang、Zhao Yang、Chengkou Liu、Wei He、Ning Zhu、Xin Li、Kai Guo

  DOI：10.1055/s-0037-1611888

  日期：2019.9

  C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments. A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling

  抽象的 开发了一种在无金属条件下通过苯乙烯与吲哚的氧化交叉偶联合成C-3二羰基吲哚的新方法。此外，获得了中等至良好产率的宽范围的C-3二羰基吲哚，并基于对照和同位素标记实验提出了一个合理的机理。 开发了一种在无金属条件下通过苯乙烯与吲哚的氧化交叉偶联合成C-3二羰基吲哚的新方法。此外，获得了中等至良好产率的宽范围的C-3二羰基吲哚，并基于对照和同位素标记实验提出了一个合理的机理。
• 一种双羰基吲哚类化合物的合成方法
  申请人：南京工业大学

  公开号：CN108863895B

  公开（公告）日：2020-10-09

  本发明公开了一种双羰基吲哚类化合物的合成方法，所述的合成方法包括将乙醛类衍生物I与吲哚衍生物II发生氧化偶联反应，得到双羰基吲哚类化合物III。本发明提供的合成方法反应高效，收率较高，绿色环保，反应条件温和，无需强酸强碱，廉价金属催化，反应底物廉价易得，适合大规模工业化生产。
• Direct Regioselective Oxidative Cross-Coupling of Indoles with Methyl Ketones: A Novel Route to C3-Dicarbonylation of Indoles
  作者：Qinghe Gao、Jingjing Zhang、Xia Wu、Shan Liu、Anxin Wu

  DOI：10.1021/ol503366r

  日期：2015.1.2

  The first C3-dicarbonylation of indoles was realized through direct oxidative cross-coupling of indoles with methyl ketones in the presence of molecular iodine and pyrrolidine. This reaction constructed a highly efficient indolyl diketones scaffold, which might be regarded as a useful biological and pharmacological tool in the exploration of therapeutic A2BAR modulators. The use of inexpensive molecular

  通过在分子碘和吡咯烷存在下吲哚与甲基酮的直接氧化交叉偶联，实现了吲哚的第一次C3-二羰基化。该反应构建了高效的吲哚基二酮支架，在探索治疗性A 2B AR调节剂中，可以将其视为有用的生物学和药理学工具。使用廉价的分子碘和吡咯烷以及广泛的底物范围使该方案非常实用。初步的机理研究表明，该过程涉及两条路径。
• Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives
  作者：Sabrina Taliani、Maria Letizia Trincavelli、Barbara Cosimelli、Sonia Laneri、Elda Severi、Elisabetta Barresi、Isabella Pugliesi、Simona Daniele、Chiara Giacomelli、Giovanni Greco、Ettore Novellino、Claudia Martini、Federico Da Settimo

  DOI：10.1016/j.ejmech.2013.09.001

  日期：2013.11

  We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A(2B) AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A(2A) and A(3) ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A(1) AR. When tested on A(2B) AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A(2B) AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs. (C) 2013 Elsevier Masson SAS. All rights reserved.