α-hydroxycinnamic acid | 5801-57-0

• 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: α-hydroxycinnamic acid
• 英文别名: 2-Hydroxy-3-phenylprop-2-enoic acid
• CAS: 5801-57-0
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: DEDGUGJNLNLJSR-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C(Solv: acetic acid (64-19-7); benzene (71-43-2))
• 沸点：
  343.7±42.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-hydroxycinnamic acid 在 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到3,8-Bis-[1-phenyl-meth-(Z)-ylidene]-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonane-2,7-dione
  参考文献：
  名称：

  Munoz, Aurelio; Lamande, Lydia, Phosphorus and Sulfur and the Related Elements, 1988, vol. 35, p. 195 - 202

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-4-(苯基亚甲基)噁唑-5(4h)-酮 在 盐酸 作用下， 生成 α-hydroxycinnamic acid
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8

文献信息

• Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors
  作者：Daniel J. Burkett、Brittney N. Wyatt、Mallory Mews、Anson Bautista、Ryan Engel、Chris Dockendorff、William A. Donaldson、Martin St. Maurice

  DOI：10.1016/j.bmc.2019.07.027

  日期：2019.9

  5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.

  通过基于结构的药物设计项目（SBDD），发现了有效的丙酮酸羧化酶小分子抑制剂（PC）。制备了一系列α-酮酸（7）和α-羟基肉桂酸（8），并在两种测定中评估了其对PC的抑制作用。两种最有效的抑制剂是3,3'-（1,4-亚苯基）双[2-羟基-2-丙酸]（8u）和2-羟基-3-（喹啉-2-基）丙酸（8v））的IC 50值分别为3.0±1.0μM和4.3±1.5μM。化合物8v是相对于丙酮酸（K i = 0.74μM）和针对ATP的混合型抑制剂，表明它靶向PC的独特羧基转移酶（CT）域。此外，化合物8v不会显着抑制人碳酸酐酶II，基质金属蛋白酶-2，苹果酸脱氢酶或乳酸脱氢酶。
• 5-Benzylidene-4-oxazolidinones potently inhibit biofilm formation in Methicillin-resistant Staphylococcus aureus
  作者：Grant A. Edwards、Nataliia V. Shymanska、Joshua G. Pierce

  DOI：10.1039/c7cc03626d

  日期：——

  Investigation into the biological function of 5-benzylidene-4-oxazolidinones revealed dose-dependent inhibition of biofilm formation in Methicillin-resistantS. aureus(MRSA).

  对5-苄基亚甲基-4-噁唑烷酮的生物功能进行的调查显示，对耐甲氧西林金黄色葡萄球菌（MRSA）的生物膜形成具有剂量依赖性的抑制作用。
• Synthesis and biological evaluation of analogues of butyrolactone I and molecular model of its interaction with CDK2
  作者：Miguel F. Braña、M. Luisa García、Berta López、Beatriz de Pascual-Teresa、Ana Ramos、Jose M. Pozuelo、M. Teresa Domínguez

  DOI：10.1039/b403052d

  日期：——

  A series of analogues of butyrolactone I, a natural product isolated from Aspergillus terreus that selectively inhibits the CDK2 and CDK1 kinases and that has been found to exhibit an interesting antiproliferative activity, have been synthesized. Its antitumor activity has been tested. Molecular models of the complex between butyrolactone I and the CDK2 active site have been built using a combination of conformational search and automated docking techniques. The stability of the resulting complexes has been assessed by molecular dynamics simulations and the experimental results obtained for the synthesized analogues are rationalized based on the molecular models.

  一系列丁酯内酯I的类似物被合成，该天然产物是从土曲霉（Aspergillus terreus）中分离出来的，能够选择性抑制CDK2和CDK1激酶，并且已被发现表现出有趣的抗增殖活性。其抗肿瘤活性已被测试。通过结合构象搜索和自动对接技术构建了丁酯内酯I与CDK2活性位点之间复合物的分子模型。通过分子动态模拟评估了所得到复合物的稳定性，并基于分子模型对合成类似物获得的实验结果进行了合理化分析。
• [EN] CARBONIC ANHYDRASE INHIBITORS<br/>[FR] INHIBITEURS D'ANHYDRASE CARBONIQUE
  申请人：UNIV GRIFFITH

  公开号：WO2018204987A1

  公开（公告）日：2018-11-15

  Compounds are provided which are inhibitors of the CAXII enzyme. Due to the interaction between CAXII and Pgp, such compounds may be useful in lowering the chemoresistance of a cancer allowing for co-administration with existing anti-cancer agents.

  提供了抑制CAXII酶的化合物。由于CAXII和Pgp之间的相互作用，这些化合物可能有助于降低癌症的化疗抗药性，从而可以与现有的抗癌药物同时使用。
• Fusion proteins between plant cell-wall degrading enzymes, and their uses
  申请人：Institut National de la Recherche Agronomique

  公开号：US07981650B2

  公开（公告）日：2011-07-19

  The invention relates to the use of fusion proteins between at least two plant cell-wall degrading enzymes, the enzymes being such that they do not contain a C-terminal carbohydrate-binding-molecule (CBM), and optionally a CBM, the enzymes and CBM being recombinant proteins corresponding to native proteins in fungi, or mutated forms thereof, for carrying out processes of plant cell-wall degradation in the frame of the preparation, from plants or vegetal by-products, of compounds of interest located in plant cell-wall, or in the frame of the bleaching of pulp and paper.

  本发明涉及使用至少两种植物细胞壁降解酶之间的融合蛋白，这些酶不含有C端糖类结合分子（CBM），以及可选的CBM，这些酶和CBM是重组蛋白，对应于真菌中的天然蛋白或其突变形式，用于在从植物或植物副产品中制备植物细胞壁中的化合物的过程中进行植物细胞壁降解，或在漂白纸浆和纸张的过程中进行。