(E)-1-(2-hydroxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one | 1443143-90-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2-hydroxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2-hydroxyphenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 1443143-90-5
• 化学式: C₁₆H₁₁F₃O₂
• 分子量: 292.257
• InChiKey: LSFPYNVKZANYQT-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.17h， 以98.6%的产率得到1-(2-hydroxy-phenyl)-3-(2-trifluoromethylphenyl)-propan-1-one
  参考文献：
  名称：

  Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study

  摘要：

  Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.013
• 作为产物：
  描述：

  邻三氟甲基苯甲醛 、 2'-羟基苯乙酮 在 Musa sp. 'Malbhog' peel ash 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以81%的产率得到(E)-1-(2-hydroxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  现有危险反应介质的生物催化绿色替代品：室温下通过Claisen-Schmidt反应合成查尔酮和黄酮衍生物

  摘要：

  由于全球废料数量的增加，将废料或次级副产品转化为用于各种应用的增值产品引起了人们的极大兴趣。在此，两种新颖的农业食品废品Musa sp。``马尔堡''果皮灰（MMPA）和Musa Champa霍特 前钩。F.果皮灰（MCPA）用作催化剂，可促进在室温下无溶剂条件下廉价，高效且生态友好的碳-碳键形成交叉羟醛反应。此外，在氧气气氛中使所得产物与这些促进剂反应，并导致形成新的黄酮衍生物。此外，使用不同的复杂分析技术，例如傅立叶变换红外光谱（FT-IR），X射线衍射法（XRD），Brunauer-Emmett-Teller分析（BET），拉曼光谱，扫描电子显微镜，对用过的催化剂进行了适当的表征。能量色散X射线光谱（SEM-EDS），过渡电子显微镜（TEM），X射线光电子能谱（XPS）和热重分析（TGA）以及使用原子吸收光谱和离子色谱法的元素检测。这两种方法均不含金属，并且不含任何额外的添加剂，助催

  DOI：

  10.1039/d0nj03839c

文献信息

• Differences in antioxidant potential of chalcones in human serum: In vitro study
  作者：Tamara Janković、Nemanja Turković、Jelena Kotur-Stevuljević、Zorica Vujić、Branka Ivković

  DOI：10.1016/j.cbi.2020.109084

  日期：2020.6

  values. Samples with Ch11 and Ch13 showed significant negative correlation between TAS and TOS (p < 0.05 for both), but in Ch14 sample the negative correlation existed between TAS and PAB (p < 0.05). CONCLUSION Lower value of OS (i.e. better antioxidative potency) was noticed in samples with Ch11-Ch15. Electron-donor effects of substituent groups as a structural part of these chalcones could explain

  引言氧化剂和抗氧化剂之间的不平衡以氧化剂为先导，可能导致损害，被称为氧化应激。酶性或非酶性抗氧化剂（AO）均可减少促氧化剂如DNA，蛋白质和脂质损伤的多种作用。Chalcones（1,3-diaryl-2-propen-1-ones）是在植物中广泛生物合成的开链类黄酮。这项研究的目的是在体外模型中（天然条件下）测试15个查耳酮（Chs）的抗氧化能力，以及外源性氧化应激。材料与方法用0.25 mmol / L叔丁基氢过氧化氢（TBH）在健康个体的血清样品中诱导氧化应激，然后我们监测了各种浓度的查耳酮对氧化应激参数的影响：总抗氧化状态（TAS），总氧化状态（TOS），巯基总浓度（SHG）和氧化前-抗氧化平衡（PAB），以及计算出的氧化前评分，抗氧化评分和氧化评分（OS）。采用非参数重复测量方差分析（Friedman's test），以天然状态和TBH影响比较具有15种不同查耳酮的样品的抗氧化能
• Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization
  作者：Zachary D. Miller、Byung Joo Lee、Tehshik P. Yoon

  DOI：10.1002/anie.201706975

  日期：2017.9.18

  Cross-products: Lewis acid catalyzed triplet sensitization enables the highly enantioselective crossed cycloaddition of chalcones and styrenes to forge cyclobutane cores. These cores are found in multiple bioactive natural products.

  交叉产物：路易斯酸催化的三重态敏化作用使查尔酮和苯乙烯具有高度对映选择性的交叉环加成反应，从而形成环丁烷核。这些核心存在于多种生物活性天然产物中。
• Biocatalytic green alternative to existing hazardous reaction media: synthesis of chalcone and flavone derivatives <i>via</i> the Claisen–Schmidt reaction at room temperature
  作者：Kashyap J. Tamuli、Ranjan K. Sahoo、Manobjyoti Bordoloi

  DOI：10.1039/d0nj03839c

  日期：——

  Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon–carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly

  由于全球废料数量的增加，将废料或次级副产品转化为用于各种应用的增值产品引起了人们的极大兴趣。在此，两种新颖的农业食品废品Musa sp。``马尔堡''果皮灰（MMPA）和Musa Champa霍特 前钩。F.果皮灰（MCPA）用作催化剂，可促进在室温下无溶剂条件下廉价，高效且生态友好的碳-碳键形成交叉羟醛反应。此外，在氧气气氛中使所得产物与这些促进剂反应，并导致形成新的黄酮衍生物。此外，使用不同的复杂分析技术，例如傅立叶变换红外光谱（FT-IR），X射线衍射法（XRD），Brunauer-Emmett-Teller分析（BET），拉曼光谱，扫描电子显微镜，对用过的催化剂进行了适当的表征。能量色散X射线光谱（SEM-EDS），过渡电子显微镜（TEM），X射线光电子能谱（XPS）和热重分析（TGA）以及使用原子吸收光谱和离子色谱法的元素检测。这两种方法均不含金属，并且不含任何额外的添加剂，助催
• Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study
  作者：Branka M. Ivković、Katarina Nikolic、Bojana B. Ilić、Željko S. Žižak、Radmila B. Novaković、Olivera A. Čudina、Sote M. Vladimirov

  DOI：10.1016/j.ejmech.2013.02.013

  日期：2013.5

  Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.