<3,4-Dimethoxy-benzyliden>-brenztraubensaeure | 65152-30-9

• 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: <3,4-Dimethoxy-benzyliden>-brenztraubensaeure
• 英文别名: 3,4-Dimethoxy-benzyliden-brenztraubensaeure；(3,4-Dimethoxy-benzyliden)-brenztraubensaeure；4-(3,4-dimethoxyphenyl)-2-oxobut-3-enoic acid
• CAS: 65152-30-9
• 化学式: C₁₂H₁₂O₅
• mdl: MFCD00034680
• 分子量: 236.224
• InChiKey: SHUJCNYJGLPHKM-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C
• 沸点：
  398.9±42.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <3,4-Dimethoxy-benzyliden>-brenztraubensaeure 在 氯仿 、 溴 作用下， 生成 4-bromo-5-(2-bromo-4,5-dimethoxy-phenyl)-3-hydroxy-5H-furan-2-one
  参考文献：
  名称：

  Particle Mass Emission Rates from Current-Technology, Light-Duty Gasoline Vehicles

  摘要：

  Now that the U.S. Environmental Protection Agency has promulgated new National Ambient Air Quality Standards for PM2.5, work will begin on generating the data required to determine the sources of ambient PM2.5 and the magnitude of their contributions to air pollution. This paper summarizes the results of an Environmental Research Consortium program, carried out under the auspices of the U.S. Council for Automotive Research. The program focused on particulate matter (PM) emissions from representative, current-technology, light-duty gasoline vehicles produced by DaimlerChrysler Corp., Ford Motor Co., and General Motors Corp. The vehicles, for the most part taken from the manufacturer's certification and durability fleets, were dynamometer-tested using the three-phase Federal Test Procedure in the companies' laboratories. The test fleet was made up of a mixture of both low-mileage (2K-35K miles) and high-mileage (60K-150K miles) cars, vans, sport utility vehicles, and light trucks. For each vehicle tested, PM emissions were accumulated over 4 cold-start tests, which were run on successive days. PM emission rates from the entire fleet (22 vehicles total) averaged less than 2 mg/mile. All 18 vehicles tested using California Phase 2 reformulated gasoline had PM emission rates less than 2 mg/mile at both low and high mileages.

  DOI：

  10.1080/10473289.2000.10464138
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 丙酮酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 <3,4-Dimethoxy-benzyliden>-brenztraubensaeure
  参考文献：
  名称：

  Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

  摘要：

  新型rel-(5R,6S,7S)-2-氧代-5,7-二芳基-3,5,6,7-四氢-2H-噻吩并[2,3-d]噻唑-6-基-氧代-乙酸在52-70%的产率下通过5-芳基亚亚甲基-4-硫代-2-噻唑烷酮与一系列芳基亚亚甲基丙酮酸的区域选择性和对映选择性异-Diels-Alder反应合成。合成的化合物在NCI60癌细胞系中进行了抗癌活性评价，并在大鼠卡拉胶水肿模型上进行了抗渗出活性评价。生物筛选数据表明3e在结肠癌HT-29细胞系中具有中等抗肿瘤活性，3b具有有希望的抗渗出效果。

  DOI：

  10.1515/hc-2014-0204

文献信息

• Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture
  作者：Christian Steuer、Christian Gege、Wolfgang Fischl、Karl H. Heinonen、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1016/j.bmc.2011.05.015

  日期：2011.7

  The development of small molecule inhibitors of the viral protease is of considerable interest for the treatment of emergent flaviviral diseases such as Dengue or West Nile fever. Until today little progress has been made in finding drug-like compounds that inhibit the protease and provide a starting point for lead optimization. We describe here the initial steps of a drug discovery effort that focused on the styryl pharmacophore, combined with a ketoamide function to serve as electrophilic trap for the catalytic serine. This resulted in a fragment-like lead compound with reasonable target affinity and good ligand efficiency, which was extensively modified to explore structure-activity relationships. Selected compounds were cross-tested against the West Nile virus protease and thrombin, indicating that selectivity for one or more flaviviral proteases can be achieved. Finally, the antiviral activity of several protease inhibitors was confirmed in a cell-culture model of Dengue virus replication. The SAR presented here may serve as starting point for further drug discovery efforts with the aim of targeting flaviviral proteases. (C) 2011 Elsevier Ltd. All rights reserved.