(E)-3-(5-(4-(trifluoromethyl)phenyl)furan-2-yl)acrylic acid | 765937-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(5-(4-(trifluoromethyl)phenyl)furan-2-yl)acrylic acid
• 英文别名: 3-[5-(4-trifluoromethylphenyl)-2-furyl]acrylic acid；(E)-3-[5-[4-(trifluoromethyl)phenyl]furan-2-yl]prop-2-enoic acid
• CAS: 765937-70-0
• 化学式: C₁₄H₉F₃O₃
• 分子量: 282.219
• InChiKey: ROJUCCZWDUNYEI-SOFGYWHQSA-N

物化性质

• 沸点：
  379.4±42.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-(4-(trifluoromethyl)phenyl)furan-2-yl)acrylic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 1.5h， 生成 2-(4-(trifluoromethyl)phenyl)furo[3,2-c]pyridin-4(5H)-one
  参考文献：
  名称：

  Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport

  摘要：

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.

  DOI：

  10.1021/jacs.5b05672
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 哌啶 、 吡啶 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 (E)-3-(5-(4-(trifluoromethyl)phenyl)furan-2-yl)acrylic acid
  参考文献：
  名称：

  非硫醇法呢基转移酶抑制剂：N-（4-甲苯基乙酰氨基-3-苯甲酰基苯基）-3-芳基呋喃基丙烯酸酰胺。

  摘要：

  我们已经设计了芳基呋喃基丙烯酸取代的二苯甲酮作为非硫醇法呢基转移酶抑制剂，利用了法呢基转移酶的新型芳基结合位点。这些化合物在低纳摩尔范围内显示活性。

  DOI：

  10.1016/j.bmc.2004.07.010

文献信息

• Non-thiol farnesyltransferase inhibitors: N-(4-tolylacetylamino-3-benzoylphenyl)-3-arylfurylacrylic acid amides
  作者：Andreas Mitsch、Pia Wißner、Katrin Silber、Peter Haebel、Isabel Sattler、Gerhard Klebe、Martin Schlitzer

  DOI：10.1016/j.bmc.2004.07.010

  日期：2004.9

  We have designed arylfurylacryl-substituted benzophenones as non-thiol farnesyltransferase inhibitors utilizing a novel aryl binding site of farnesyltransferase. These compounds display activity in the low nanomolar range.

  我们已经设计了芳基呋喃基丙烯酸取代的二苯甲酮作为非硫醇法呢基转移酶抑制剂，利用了法呢基转移酶的新型芳基结合位点。这些化合物在低纳摩尔范围内显示活性。
• Wiesner; Mitsch; Altenkaemper, Pharmazie, 2003, vol. 58, # 12, p. 854 - 856
  作者：Wiesner、Mitsch、Altenkaemper、Ortmann、Jomaa、Schlitzer, Martin

  DOI：——

  日期：——
• Structure–activity relationships of novel anti-malarial agents. Part 7: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides with polar moieties
  作者：Jochen Wiesner、Andreas Mitsch、Hassan Jomaa、Martin Schlitzer

  DOI：10.1016/s0960-894x(03)00353-6

  日期：2003.7

  In a previous report, we have provided evidence that novel anti-malarial compounds based on 2,5-diaminobenzophenone farnesyltransferase inhibitors might benefit from the presence of a polar moiety at the para position of the terminal phenyl of the arylfurylacryloyl partial structure. Here, we demonstrate that different moieties with hydrogen bond acceptor properties lead to equipotent or even improved anti-malarial activity in comparison to the nitro group described before. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport
  作者：Takuya Terai、Moe Kohno、Gaelle Boncompain、Shigeru Sugiyama、Nae Saito、Ryo Fujikake、Tasuku Ueno、Toru Komatsu、Kenjiro Hanaoka、Takayoshi Okabe、Yasuteru Urano、Franck Perez、Tetsuo Nagano

  DOI：10.1021/jacs.5b05672

  日期：2015.8.26

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.