3-(5-bromo-2-methoxy-phenyl)-2-cyano-ethyl acrylate | 199179-13-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(5-bromo-2-methoxy-phenyl)-2-cyano-ethyl acrylate
• 英文别名: ethyl 3-(5-bromo-2-methoxy-phenyl)-2-cyanoacrylate；Ethyl 3-(5-bromo-2-methoxyphenyl)-2-cyanoprop-2-enoate
• CAS: 199179-13-0
• 化学式: C₁₃H₁₂BrNO₃
• mdl: MFCD00158932
• 分子量: 310.147
• InChiKey: MJEHPFMLBAQNRU-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethanol (64-17-5))
• 沸点：
  419.6±45.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-methoxy-phenyl)-2-cyano-ethyl acrylate 在 吡啶 、 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 33.0h， 生成 3-(4-Bromo-benzyl)-5-[1-(5-bromo-2-methoxy-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  Brandao; Andrade; Pereira, Heterocyclic Communications, 2004, vol. 10, # 1, p. 9 - 14

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲醛 、 氰乙酸乙酯 在 吡啶 作用下， 以 苯 为溶剂， 反应 10.0h， 以67%的产率得到3-(5-bromo-2-methoxy-phenyl)-2-cyano-ethyl acrylate
  参考文献：
  名称：

  Brandao; Andrade; Pereira, Heterocyclic Communications, 2004, vol. 10, # 1, p. 9 - 14

  摘要：

  DOI：

文献信息

• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，
• SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF NEW THIAZOLIDINE-2,4-DIONES, 4-THIOXOTHIAZOLIDINONES AND 2-THIOXOIMIDAZOLIDINONES
  作者：L.C. SANTOS、F.T. UCHŌA、A.R.P.A. CANAS、I.A. SOUSA、R.O. MOURA、M.C.A. LIMA、S.L. GALDINO、I.R. PITTA、J. BARBE

  DOI：10.1515/hc.2005.11.2.121

  日期：2005.1

  compounds. In particular thiazolidines are known to show anti-inflammatory activity. With reference to this, synthesis of some 5-benzylidene-thioxoimidazolidinones and thioxothiazolidinones substituted at the position 3 by a benzyl (or phenacyl) group, were reported in previous papers [3-5]. Synthesis and physicochemical data of new 5-benzylidene-3-(4-chlorobenzyl)thiazolidine-2,4-diones 8-10 or 5-(l//

  新的亚苄基咪唑烷和噻唑烷衍生物是通过在氰基丙烯酸酯上由取代的硫代咪唑烷酮、噻唑烷二酮和硫代噻唑烷酮亲核加成而制备的。通过角叉菜胶诱导的爪水肿试验评价合成的噻唑烷的抗炎活性。简介 由于它们的药理特性 [1,2]，咪唑烷二酮和噻唑烷二酮是被广泛研究的化合物。特别是已知噻唑烷显示抗炎活性。与此相关，一些5-亚苄基-硫代咪唑烷酮和3位被苄基（或苯甲酰基）取代的硫代噻唑烷酮的合成在以前的论文中有所报道[3-5]。新型5-benzylidene-3-(4-chlorobenzyl)thiazolidine-2的合成及理化数据，4-二酮 8-10 或 5-(l//-indol-3-yl-methylene)-3-(4-chlorobenzyl)-4-thioxo-thiazolidin2-one 11（图 1）如下所示。这些化合物是从 3-(4-chlorobenzyl)thiazolidine-2,4-dione
• Synthesis and Biological Activity of Novel Acridinylidene and Benzylidene thiazolidinediones
  作者：R.H. Mourão、T.G. Silva、A.L.M. Soares、E.S. Vieira、J.N. Santos、M.C.A. Lima、V.L.M. Lima、S.L. Galdino、J. Barbe、I.R. Pitta

  DOI：10.1016/j.ejmech.2005.06.002

  日期：2005.11

  A novel set of acridinylidene thiazolidinediones and benzylidene thiazolidinediones was synthesized by nucleophilic addition of cyanoacrylates. Some of these compounds were evaluated for their glucose lowering capability and their effects on the triglyceride level in alloxan diabetic mice. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands
  作者：Cleiton Diniz Barros、Angélica Amorim Amato、Tiago Bento de Oliveira、Karime Bicas Rocha Iannini、Anekécia Lauro da Silva、Teresinha Gonçalves da Silva、Elisa Soares Leite、Marcelo Zaldini Hernandes、Maria do Carmo Alves de Lima、Suely Lins Galdino、Francisco de Assis Rocha Neves、Ivan da Rocha Pitta

  DOI：10.1016/j.bmc.2010.04.045

  日期：2010.6

  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.
• Albuquerque; Silva; Pitta, Pharmazie, 2005, vol. 60, # 1, p. 13 - 17
  作者：Albuquerque、Silva、Pitta、Silva、Silva、Malagueno、Santana、Wanderley、Lima、Galdino、Barbe、Pitta, Ivan Rocha

  DOI：——

  日期：——