(E)-1-(4-methoxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one | 1164497-46-4

• 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-(4-methoxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: 1-(4-Methoxyphenyl)-3-[2-(trifluoromethyl)phenyl]-2-propen-1-one；(E)-1-(4-methoxyphenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 1164497-46-4
• 化学式: C₁₇H₁₃F₃O₂
• 分子量: 306.284
• InChiKey: IUJWAWAODSXWTI-DHZHZOJOSA-N

物化性质

• 熔点：
  50.6-50.8 °C
• 沸点：
  394.5±42.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻三氟甲基苯甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以70.8%的产率得到(E)-1-(4-methoxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型合成查尔酮衍生物作为抗炎药的评价和发现

  摘要：

  事实证明，主要的抗炎药，类固醇和环氧合酶具有严重的副作用。在这里，合成了一系列查尔酮衍生物，并筛选了抗炎活性。QSAR研究表明，查耳酮的B环中有吸电子基团，而A环中有供电子基团对于抑制LPS诱导的IL-6表达很重要。此外，化合物22，23，26，40，和47抑制TNF-α和IL-6释放的剂量依赖的方式和降低LPS诱导的TNF-α，IL-1β，IL-6，IL-12，和COX-2 mRNA的产生。从机械上讲，化合物23和26干扰JNK /NF-κB信号传导并剂量依赖性地阻止ERK和p38激活。另外，23和26对LPS诱导的死亡显示出显着的保护作用，并且能够阻断巨噬细胞中高葡萄糖激活的细胞因子谱。总之，这些数据显示了一系列在炎性疾病中具有潜在治疗作用的抗炎查耳酮。

  DOI：

  10.1021/jm200946h

文献信息

• Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: Synthesis, biochemistry and molecular docking studies
  作者：Bijo Mathew、Githa Elizabeth Mathew、Gülberk Uçar、Ipek Baysal、Jerad Suresh、Jobin Kunjumon Vilapurathu、Aneesh Prakasan、Jeethu Kuruppath Suresh、Anjana Thomas

  DOI：10.1016/j.bioorg.2015.07.001

  日期：2015.10

  mode of inhibition. The most potent compound (2E)-1-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl] prop-2-en-1-one showed the best activity and higher selectivity towards hMAO-B with Ki and SI values of 0.22 ± 0.01 μM and 0.05 comparable to that standard drug, Selegiline Ki and SI values were found as 0.33 ± 0.03 μM and 0.04, respectively. Molecular docking studies were carried out to further explain

  合成了一系列具有氟和三氟甲基衍生物的甲氧基化查耳酮，并研究了它们抑制人单胺氧化酶A和B的能力。已通过其1 H NMR，13 C NMR，质谱数据对化合物的化学结构进行了表征。和元素分析。结果表明，这些化合物是具有竞争性抑制方式的可逆和选择性MAO-B抑制剂。最有效的化合物（2 ë）-1-（4-甲氧基苯基）-3- [4-（三氟甲基）苯基〕丙-2-烯-1-酮向显示hMAO-B具有最佳的活性和更高的选择性ķ我和SI值分别为0.22±0.01μM和0.05，与标准药物Selegiline K相当i和SI值分别为0.33±0.03μM和0.04。进行了分子对接研究，以进一步解释新化合物的体外结果，并确定hMAO-B抑制剂结合腔内化合物的假设结合模式。
• [EN] NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER<br/>[FR] MODULATEURS DE RÉCEPTEURS NUCLÉAIRES ET LEUR UTILISATION POUR LE TRAITEMENT ET LA PRÉVENTION D'UN CANCER
  申请人：US HEALTH

  公开号：WO2012174436A1

  公开（公告）日：2012-12-20

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

  本文披露了一些化合物，它们是核受体调节剂，可以作为雄激素受体的拮抗剂，例如，公式I的化合物：其中R1至R5和X1至X5如本文所述，以及其药用盐、溶剂化合物和立体异构体。还披露了包括这些化合物的药物组合物，以及使用方法和治疗癌症，包括前列腺癌、其他核受体介导的癌症和其他疾病的方法。
• NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER
  申请人：The U.S.A. as represented by the Secretary, Department of Health and Human Services

  公开号：EP3333153A1

  公开（公告）日：2018-06-13

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

  所公开的化合物是核受体调节剂，可作为雄激素受体的拮抗剂，例如，式 I 的化合物： 其中 R1 至 R5 和 X1 至 X5 如本文所述，以及其药学上可接受的盐、溶剂和立体异构体。此外，还公开了包含此类化合物的药物组合物，以及使用方法和癌症（包括前列腺癌、其他核受体介导的癌症和其他疾病）的治疗方法。
• Nuclear receptor modulators and their use for the treatment and prevention of cancer
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Services

  公开号：US10737995B2

  公开（公告）日：2020-08-11

  Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

  所公开的化合物是核受体调节剂，可作为雄激素受体的拮抗剂，例如，式 I 的化合物： 其中 R1 至 R5 和 X1 至 X5 如本文所述，以及其药学上可接受的盐、溶剂和立体异构体。此外，还公开了包含此类化合物的药物组合物、使用方法以及癌症（包括前列腺癌）、其他核受体介导的癌症和其他疾病的治疗方法。
• Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors
  作者：Ji Won Choi、Bo Ko Jang、Nam-chul Cho、Jong-Hyun Park、Seul Ki Yeon、Eun Ji Ju、Yong Sup Lee、Gyoonhee Han、Ae Nim Pae、Dong Jin Kim、Ki Duk Park

  DOI：10.1016/j.bmc.2015.08.012

  日期：2015.10

  We have synthesized three categories of alpha,beta-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including alpha, beta-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC50 human MAO-B 16 nM, >6000-fold selective vs MAO-A) and compound 10b exhibited good reversibility compared with selegiline, a well-known irreversible MAO-B inhibitor. However, both a, b-unsaturated amide and ester derivatives exhibited weaker MAO-B inhibition potencies. The docking studies provided insights into the possible binding modes and the key interaction sites of the synthesized MAO-B inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.