ethyl (perfluorophenyl) fumarate | 1419884-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: ethyl (perfluorophenyl) fumarate
• 英文别名: Fumaric acid, ethyl pentafluorophenyl ester；1-O-ethyl 4-O-(2,3,4,5,6-pentafluorophenyl) (E)-but-2-enedioate
• CAS: 1419884-98-2
• 化学式: C₁₂H₇F₅O₄
• 分子量: 310.177
• InChiKey: QNRCXECFFIGWRM-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  喹啉-3-碳酰肼 、 ethyl (perfluorophenyl) fumarate 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以51%的产率得到ethyl (E)-4-oxo-4-[2-(quinoline-3-carbonyl)hydrazinyl]but-2-enoate
  参考文献：
  名称：

  Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion

  摘要：

  翻译结果： 对缺氧诱导因子（HIF）脯氨酰羟化酶（PHD或EGLN酶）的抑制在治疗贫血和缺血相关疾病方面备受关注。大多数PHD抑制剂通过结合单个亚铁离子并与2-氧代戊二酸（2OG）共底物竞争结合PHD活性位点来发挥作用。非特异性铁螯合剂也能在体外和细胞内抑制PHD。我们报告了双作用PHD抑制剂的鉴定，这些抑制剂不仅与活性位点的铁结合，还能诱导在活性位点上结合第二个铁离子。通过对小分子铁络合物的分析并在非变性蛋白质谱法中评估PHD2·铁·抑制剂的比例后，鉴定出某些二酰基联氨为诱导第二个铁离子结合的PHD2抑制剂。有些化合物被证明能抑制人类肝癌和肾癌细胞系中的HIF羟化酶。

  DOI：

  10.1039/c2ob26648b
• 作为产物：
  描述：

  五氟苯酚 、 富马酸单乙酯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到ethyl (perfluorophenyl) fumarate
  参考文献：
  名称：

  Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion

  摘要：

  翻译结果： 对缺氧诱导因子（HIF）脯氨酰羟化酶（PHD或EGLN酶）的抑制在治疗贫血和缺血相关疾病方面备受关注。大多数PHD抑制剂通过结合单个亚铁离子并与2-氧代戊二酸（2OG）共底物竞争结合PHD活性位点来发挥作用。非特异性铁螯合剂也能在体外和细胞内抑制PHD。我们报告了双作用PHD抑制剂的鉴定，这些抑制剂不仅与活性位点的铁结合，还能诱导在活性位点上结合第二个铁离子。通过对小分子铁络合物的分析并在非变性蛋白质谱法中评估PHD2·铁·抑制剂的比例后，鉴定出某些二酰基联氨为诱导第二个铁离子结合的PHD2抑制剂。有些化合物被证明能抑制人类肝癌和肾癌细胞系中的HIF羟化酶。

  DOI：

  10.1039/c2ob26648b

文献信息

• Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters
  作者：Byungjun Kim、Yuna Song、Sarah Yunmi Lee

  DOI：10.1039/d1cc04875a

  日期：——

  We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1

  我们在这里报告了一种银催化的方法，用于具有多个立体中心的手性焦谷氨酸酯的对映和非对映发散合成。该过程通过将甘氨酸亚胺酯不对称共轭加成到范围广泛的 β-取代的 α,β-不饱和全氟苯基酯，然后进行内酰胺化来进行。通过利用 1,4-加成过程的催化剂控制和立体定向性，可以以高立体选择性获得所有包含两个相邻立体中心的四种产物立体异构体。
• Organocatalytic Enantio‐ and Diastereoselective Diels‐Alder Reaction between 2,4‐Dienals and α,β‐Unsaturated Esters
  作者：Byungjun Kim、Sukwoo Lee、Sarah Yunmi Lee

  DOI：10.1002/adsc.202300756

  日期：2023.11.21

  in the development of catalytic asymmetric Diels-Alder reactions, introducing α,β-unsaturated esters as dienophiles remains challenging owing to their low reactivity. Herein, we report that a chiral aminocatalyst in conjunction with a chiral isothiourea catalyst or a Brønsted acid can promote enantio- and diastereoselective Diels-Alder reactions between 2,4-dienals and α,β-unsaturated esters. This

  尽管催化不对称狄尔斯-阿尔德反应的发展取得了进展，但引入α,β-不饱和酯作为亲二烯体仍然具有挑战性，因为它们的反应活性较低。在此，我们报道手性氨基催化剂与手性异硫脲催化剂或布朗斯台德酸结合可以促进2,4-二醛和α,β-不饱和酯之间的对映选择性和非对映选择性狄尔斯-阿尔德反应。该方法通过形成手性三烯胺中间体来与活化的亲二烯体、α,β-不饱和酰基铵物质或质子化的N-杂芳基取代的烯烃进行外环加成。通过二烯和酯亲二烯体的协同活化，可以得到具有多个立构中心的密集官能化环己烯，其dr高达>25:1，ee>99%。此外，我们表明手性催化剂的构型和烯烃几何形状的变化允许对映体纯外型产物的四种立体异构体的立体发散制备。
• Structural Basis for Inhibition of the Fat Mass and Obesity Associated Protein (FTO)
  作者：WeiShen Aik、Marina Demetriades、Muhammad K. K. Hamdan、Eleanor. A. L. Bagg、Kar Kheng Yeoh、Clarisse Lejeune、Zhihong Zhang、Michael A. McDonough、Christopher J. Schofield

  DOI：10.1021/jm400193d

  日期：2013.5.9

  The fat mass and obesity associated protein (FTO) is a potential target for anti-obesity medicines. FTO is a 2-oxoglutarate (2OG)-dependent N-methyl nucleic acid demethylase that acts on substrates including 3-methylthymidine, 3-methyluracil, and 6-methyladenine. To identify FTO inhibitors, we screened a set of 2OG analogues and related compounds using differential scanning fluorometry- and liquid chromatography-based assays. The results revealed sets of both cyclic and acyclic 2OG analogues that are FTO inhibitors. Identified inhibitors include small molecules that have been used in clinical studies for the inhibition of other 2OG oxygenases. Crystallo-graphic analyses reveal inhibition by 2OG cosubstrate or primary substrate competitors as well as compounds that bind across both cosubstrate and primary substrate binding sites. The results will aid the development of more potent and selective FTO inhibitors.
• Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion
  作者：Kar Kheng Yeoh、Mun Chiang Chan、Armin Thalhammer、Marina Demetriades、Rasheduzzaman Chowdhury、Ya-Min Tian、Ineke Stolze、Luke A. McNeill、Myung Kyu Lee、Esther C. Y. Woon、Mukram M. Mackeen、Akane Kawamura、Peter J. Ratcliffe、Jasmin Mecinović、Christopher J. Schofield

  DOI：10.1039/c2ob26648b

  日期：——

  Inhibition of the hypoxia-inducible factor (HIF) prolyl hydroxylases (PHD or EGLN enzymes) is of interest for the treatment of anemia and ischemia-related diseases. Most PHD inhibitors work by binding to the single ferrous ion and competing with 2-oxoglutarate (2OG) co-substrate for binding at the PHD active site. Non-specific iron chelators also inhibit the PHDs, both in vitro and in cells. We report the identification of dual action PHD inhibitors, which bind to the active site iron and also induce the binding of a second iron ion at the active site. Following analysis of small-molecule iron complexes and application of non-denaturing protein mass spectrometry to assess PHD2·iron·inhibitor stoichiometry, selected diacylhydrazines were identified as PHD2 inhibitors that induce the binding of a second iron ion. Some compounds were shown to inhibit the HIF hydroxylases in human hepatoma and renal carcinoma cell lines.

  翻译结果： 对缺氧诱导因子（HIF）脯氨酰羟化酶（PHD或EGLN酶）的抑制在治疗贫血和缺血相关疾病方面备受关注。大多数PHD抑制剂通过结合单个亚铁离子并与2-氧代戊二酸（2OG）共底物竞争结合PHD活性位点来发挥作用。非特异性铁螯合剂也能在体外和细胞内抑制PHD。我们报告了双作用PHD抑制剂的鉴定，这些抑制剂不仅与活性位点的铁结合，还能诱导在活性位点上结合第二个铁离子。通过对小分子铁络合物的分析并在非变性蛋白质谱法中评估PHD2·铁·抑制剂的比例后，鉴定出某些二酰基联氨为诱导第二个铁离子结合的PHD2抑制剂。有些化合物被证明能抑制人类肝癌和肾癌细胞系中的HIF羟化酶。