2-丙烯-1-酮,3-(4-氟苯基)-1-(3,4,5-三甲氧苯基)-,(2E)- | 127034-06-4

• 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
• 中文名称: 2-丙烯-1-酮,3-(4-氟苯基)-1-(3,4,5-三甲氧苯基)-,(2E)-
• 英文名称: (2E)-3-(4-fluorophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-fluorophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 127034-06-4
• 化学式: C₁₈H₁₇FO₄
• 分子量: 316.329
• InChiKey: FVYXBSVIQZHXBW-RMKNXTFCSA-N

物化性质

• 熔点：
  122-125 °C
• 沸点：
  464.3±45.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-丙烯-1-酮,3-(4-氟苯基)-1-(3,4,5-三甲氧苯基)-,(2E)- 在 sodium hydroxide 、 双氧水 作用下， 生成 Methanone, [3-(4-fluorophenyl)oxiranyl](3,4,5-trimethoxyphenyl)-
  参考文献：
  名称：

  Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents

  摘要：

  A series of substituted chalcones and their corresponding pyrazoles were synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 93 compounds screened, 8 compounds, 1s, 3i,j,n, 4i,j,n and 4s, showed marked activity. Compounds 4j,n and 4s were found to be the most promising in this study. SAR is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.121
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 对氟苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以77%的产率得到2-丙烯-1-酮,3-(4-氟苯基)-1-(3,4,5-三甲氧苯基)-,(2E)-
  参考文献：
  名称：

  3'，4'，5'-三甲氧基查尔酮类似物作为一氧化氮生成和肿瘤细胞增殖抑制剂的合成和生物学评估

  摘要：

  合成了一系列23 3'，4'，5'-三甲氧基查耳酮类似物，它们对LPS /IFN-γ处理的巨噬细胞中一氧化氮（NO）的抑制作用，并研究了肿瘤细胞的增殖。4-羟基-3,3'，4'，5'-四甲氧基查尔酮（7），3,4-二羟基-3'，4'，5'-三甲氧基查尔酮（11），3-羟基-3'，4,4 '，5'-四甲氧基查耳酮（14）和3,3'，4'，5'-四甲氧基查耳酮（15）是产生NO最有效的生长抑制剂，IC 50值为0.3、1.5、1.3和0.3分别为μM。肿瘤细胞增殖测定结果表明，几种化合物对不同的癌细胞系表现出有效的抑制活性。查尔酮15是该系列中最有效的抗增殖化合物，对肝癌Hep G2和结肠癌Colon 205细胞系的IC 50值分别为1.8和2.2μM。2,3,3'，4'，5'-五甲氧基查耳酮（1），3,3'，4,4'，5,5'-六甲氧基查耳酮（3），2,3'，4,4'，5， 5'-六甲氧基查耳酮（5），2-羟基-3

  DOI：

  10.1016/j.bmc.2009.10.022

文献信息

• A novel series of benzothiazepine derivatives as tubulin polymerization inhibitors with anti-tumor potency
  作者：Bin Wang、Li-Ren Wang、Lu-Lu Liu、Wei Wang、Ruo-Jun Man、Da-Jun Zheng、Yu-Shan Deng、Yu-Shun Yang、Chen Xu、Hai-Liang Zhu

  DOI：10.1016/j.bioorg.2020.104585

  日期：2021.3

  In this work, a series of diaryl benzo[b][1,4]thiazepine derivatives D1-D36 were synthesized and screened as tubulin polymerization inhibitors with anti-tumor potency. They were designed by introducing the seven-member ring benzothiazepine as the linker for CA-4 modification for the first time. Among them, the hit compound D8 showed potential on inhibiting the growth of several cancer cell lines (IC50

  在这项工作中，合成并筛选了一系列二芳基苯并[ b ] [1,4] 硫氮杂衍生物D1-D36作为具有抗肿瘤效力的微管蛋白聚合抑制剂。它们是通过首次引入七元环苯并噻嗪作为 CA-4 修饰的接头而设计的。其中，命中化合物D8显示出抑制多种癌细胞系生长的潜力（IC 50值：HeLa 1.48 μM，MCF-7 1.47 μM，HT29 1.52 μM 和 A549 1.94 μM），与阳性对照秋水仙碱和CA-4P。D8的计算 IC 50值作为微管蛋白聚合抑制剂的浓度为 1.20 μM。流式细胞术检测结果表明，D8可以诱导有丝分裂灾难和活癌细胞的死亡。D8还表明了抗血管活性。对接模拟暗示了可能的结合模式，推断引入与附近微管蛋白链相互作用的可能性。由于新的结构试验已经进行了初步讨论，这项工作可能会激发进一步修改微管蛋白相关抗癌药物和治疗方法的新思路。
• Design, synthesis and cytotoxic activity of certain novel chalcone analogous compounds
  作者：S. El-Meligie、Azza T. Taher、Aliaa M. Kamal、A. Youssef

  DOI：10.1016/j.ejmech.2016.09.099

  日期：2017.1

  of chalcone analogous compounds were designed and synthesized. Replacing/substituting the enone or ethylenic bridge of the parent chalcone with rigid heterocyclic moieties or substituted aromatic amines gave nineteen target compounds. Their cytotoxic activities were screened against both breast and liver cancer cells as well as breast and liver normal cells. Target compounds were also evaluated for

  设计并合成了一系列查尔酮类似化合物。用刚性杂环部分或取代的芳族胺取代/取代母体查尔酮的烯酮或烯键，得到十九种目标化合物。筛选了针对乳腺癌和肝癌细胞以及乳腺癌和肝正常细胞的细胞毒性活性。还评估了目标化合物对微管蛋白β聚合的抑制活性。目标化合物2e，3a，3b，3c，4a-4d，5a，5b和6显示出对MCF-7和HepG2均具有广谱优异的抗癌活性。化合物4a显示出最大的TUBb抑制活性。
• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。
• Trimethoxy Crown Chalcones as Multifunctional Class of Monoamine Oxidase Enzyme Inhibitors
  作者：Naseer Maliyakkal、Gulberk Ucar、Bijo Mathew、Ipek Baysal、Anandkumar Tengli、Mohammad Ali Abdullah Almoyad、Della Grace Thomas Parambi、Nicola Gambacorta、Orazio Nicolotti、Asmy Appadath Beeran

  DOI：10.2174/1386207324666210603125452

  日期：2022.7

  Chalcones with methoxy substituent are considered as a promising framework for the inhibition of monoamine oxidase (MAO) enzymes.

  A series of nine trimethoxy substituted chalcones (TMa-TMi) was synthesized and evaluated as a multifunctional class of MAO inhibitors. All the synthesized compounds were investigated for their in vitro MAO inhibition, kinetics, reversibility, blood-brain barrier (BBB) permeation, and cytotoxicity and antioxidant potentials.

  In the present study, compound (2E)-3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop- 2-en-1-one (TMf) was provided with a MAO-A inhibition constant value equal to 3.47±0.09 μM with a selectivity of 0.008, thus comparable to that of moclobemide, a well known potent hMAOA inhibitor (SI=0.010). Compound (2E)-3-(4-bromophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2- en-1-one (TMh) show good MAO-B inhibition with inhibition constant of 0.46±0.009 μM. The PAMPA assay demonstrated that all the synthesized derivatives can cross the BBB successfully. The cytotoxicity studies revealed that TMf and TMh have 88.22 and 80.18 % cell viability at 25 μM. Compound TMf appeared as the most promising antioxidant molecule with IC50 values, relative to DPPH and H2O2 radical activities equal to 6.02±0.17 and 7.25±0.07 μM. To shed light on the molecular interactions of TMf and TMh towards MAO-A and MAO-B, molecular docking simulations and MM/GBSA calculations have been carried out.

  The lead molecules TMf and TMh with multi-functional nature can be further employed for the treatment of various neurodegenerative disorders and depressive states.

  背景： 具有甲氧基取代基的查耳酮被认为是一种有前途的 抑制单胺氧化酶 (MAO) 的框架。 研究方法： 合成了九种三甲氧基取代的查耳酮（TMa-TMi）系列，并将其作为一种多功能 MAO 作为一种多功能 MAO 抑制剂进行了评估。对所有合成的化合物进行了 的体外 MAO 抑制、动力学、可逆性、血脑屏障（BBB）渗透性和细胞毒性进行了研究。 渗透性、细胞毒性和抗氧化潜力进行了研究。 研究结果 在本研究中，化合物 (2E)-3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop- 2-烯-1-酮（TMf）的 MAO-A 抑制常数为 3.47±0.09 μM 选择性为 0.008，因此与众所周知的强效 hMAOA 抑制剂吗氯贝胺相当（SI=0.008）。 的选择性相当（SI=0.010）。化合物(2E)-3-(4-溴苯基)-1-(3,4,5-三甲氧基苯基)丙-2-烯-1-酮（TMh 烯-1-酮（TMh）对 MAO-B 有良好的抑制作用，抑制常数为 0.46±0.009 μM。PAMPA PAMPA 试验表明，所有合成的衍生物都能成功穿过 BBB。 细胞毒性研究表明，TMf 和 TMh 的细胞存活率分别为 88.22% 和 80.18%，在 25 微米。化合物 TMf 是最有前途的抗氧化分子，其 IC50 值为 分别为 6.02±0.17 和 7.25±0.07 μM。为了揭示 为揭示 TMf 和 TMh 对 MAO-A 和 MAO-B 的分子相互作用，进行了分子对接模拟和 MM/GBSA 计算。 模拟和 MM/GBSA 计算。 研究结论 具有多功能性质的先导分子 TMf 和 TMh 可以进一步 用于治疗各种神经退行性疾病和抑郁状态。
• Chalcones: a new class of antimitotic agents
  作者：Michael L. Edwards、David M. Stemerick、Prasad S. Sunkara

  DOI：10.1021/jm00169a021

  日期：1990.7

  A series of chalcones was evaluated as antimitotic agents. One of these, (E)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-methyl-2-pr open- 1-one) (73), was found to be an effective antimitotic agent at a concentration of 4 nM in an in vitro HeLa cell test system. When evaluated in experimental tumor models in vivo, this compound exhibited antitumor activity against L1210 leukemia and B16 melanoma.