ethyl 3-(9H-fluoren-2-yl)-2-cyanoacrylate | 142275-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ethyl 3-(9H-fluoren-2-yl)-2-cyanoacrylate
• CAS: 142275-84-1
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: FMSWIQAQKTUUCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-chloro-benzyl-thiazolidine-2,4-dione 、 ethyl 3-(9H-fluoren-2-yl)-2-cyanoacrylate 在 哌啶 作用下， 以 乙醇 为溶剂， 以81%的产率得到3-(3-chloro-benzyl)-5-(9H-fluoren-2-yl-methylene)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands

  摘要：

  Eight new 5-arylidene-3-benzyl-thiazolidine-2,4-diones with halide groups on their benzyl rings were synthesized and assayed in vivo to investigate their anti-inflammatory activities. These compounds showed considerable biological efficacy when compared to rosiglitazone, a potent and well-known agonist of PPAR gamma, which was used as a reference drug. This suggests that the substituted 5-arylidene and 3-benzylidene groups play important roles in the anti-inflammatory properties of this class of compounds. Docking studies with these compounds indicated that they exhibit specific interactions with key residues located in the site of the PPAR gamma structure, which corroborates the hypothesis that these molecules are potential ligands of PPAR gamma. In addition, competition binding assays showed that four of these compounds bound directly to the ligand-binding domain of PPAR gamma, with reduced affinity when compared to rosiglitazone. An important trend was observed between the docking scores and the anti-inflammatory activities of this set of molecules. The analysis of the docking results, which takes into account the hydrophilic and hydrophobic interactions between the ligands and the target, explained why the 3-(2-bromobenzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione compound had the best activity and the best docking score. Almost all of the stronger hydrophilic interactions occurred between the substituted 5-arylidene group of this compound and the residues of the binding site. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.045
• 作为产物：
  描述：

  2-氟萘烯甲醛 、 氰乙酸乙酯 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以34 %的产率得到ethyl 3-(9H-fluoren-2-yl)-2-cyanoacrylate
  参考文献：
  名称：

  Simple Donor–π–Acceptor Compounds Exhibiting Aggregation-Induced Emission as Hidden Fingerprints Detecting Agents

  摘要：

  对于法庭专家来说，隐性指纹是一种重要的信息载体。要检测这类法医痕迹，需要一种易于使用、结构紧凑、用途广泛的方法。这项研究旨在调查供体-π-受体系统发光物质的物理化学特性，以了解它们在检测隐性指纹方面的潜在用途。在研究过程中，设计并成功合成了一组由 (-CH=C(CN)(COOR)) 分子组成的芴化合物。研究了其光学、电化学和聚集诱导发射特性。在四氢呋喃（良好溶剂）和水（不良溶剂）的混合物中，研究了化合物的聚集诱导发射，水的比例从 0% 到 99% 不等。由于分子结构的不同，物质对有机痕量的亲和力也不同。结果发现，所有化合物都显示出 AIE 现象，而在对潜在指纹进行测试时，发现有两种物质在这一领域具有特别前瞻性的特征。

  DOI：

  10.3390/molecules28227597

文献信息

• Matsuoka, M.; Takao, M.; Kitao, T., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 182, p. 71 - 79
  作者：Matsuoka, M.、Takao, M.、Kitao, T.、Fujiwara, T.、Nakatsu, K.

  DOI：——

  日期：——