(E)-3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 127033-98-1

• 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)-3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(2-bromophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；3-phenyl-1-(3,4,5-trimethoxyphenyl)-trans-prop-2-en-1-one；3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-3’,4’,5’-trimethoxychalcone；3’,4’,5’-trimethoxychalcone；(E)-3-phenyl-1-(3,4,5-trimethoxyphenyl)-3-phenylprop-2-en-1-one；(E)-3-phenyl-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one；(2E)-3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-3-(5-bromo-2-hydroxyphenyl)-1phenylprop-2-en-1-one；3',4',5'-trimethoxy-chalcone；3',4',5'-Trimethoxy-chalkon
• CAS: 127033-98-1
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: HJRVQVGPAQZDPJ-MDZDMXLPSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  465.7±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 乙醇 、 溶剂黄146 、 铂 作用下， 生成 N-[1-phenyl-3-(3,4,5-trimethoxy-phenyl)-propyl]-acetamide
  参考文献：
  名称：

  Lettre; Fernholz, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1943, vol. 278, p. 175,197

  摘要：

  DOI：
• 作为产物：
  描述：

  5-异丙烯基-1,2,3-三甲氧基-苯 在 氢氧化钾 、 臭氧 、 溶剂黄146 作用下， 生成 (E)-3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Bogert; Isham, Journal of the American Chemical Society, 1914, vol. 36, p. 518

  摘要：

  DOI：

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。
• [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。
• Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans
  作者：D. Batovska、St. Parushev、A. Slavova、V. Bankova、I. Tsvetkova、M. Ninova、H. Najdenski

  DOI：10.1016/j.ejmech.2006.08.012

  日期：2007.1

  A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location

  合成了大量查耳酮，并研究了其对白色念珠菌的活性。SAR分析表明，抗真菌活性高度依赖于芳基环的取代方式，并在很大程度上与化合物与巯基相互作用的能力有关。最具活性的是羟基化查耳酮，因为它们的活性与芳基环B中酚基的位置有关，如下所示：o-OH> p-OH约为3,4-di-OH> m-OH。获得的这些相关性和其他相关性极大地有助于设计抗候选查耳酮。
• Methoxychalcones: Effect of Methoxyl Group on the Antifungal, Antibacterial and Antiproliferative Activities
  作者：Beatriz C. Marques、Mariana B. Santos、Daiane B. Anselmo、Diego A. Monteiro、Eleni Gomes、Marilia F.C. Saiki、Paula Rahal、Pedro L. Rosalen、Janaina C.O. Sardi、Luis O. Regasini

  DOI：10.2174/1573406415666190724145158

  日期：2020.11.6

  general, chalcones of series I are the most potent antifungal, antibacterial and antiproliferative agents. 2',4',5'-Trimethoxychalcone (11) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 µg/mL), eight times more potent than fluconazole (reference antifungal drug). 3'-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 µg/mL). 2',5'-Dimethoxychalcone (9) displayed

  背景技术被甲氧基取代的查耳酮具有广泛的生物活性，包括抗真菌，抗菌和抗增殖作用。然而，尚未描述关于该取代基在查耳酮骨架上的相关性的明确和明确的研究。目的这项工作的目的是评估两个系列的十七种合成的区域异构甲氧基查耳酮的抑菌，抗真菌和抗增殖活性。系列I和II由分别被环A（5-12）和B（13-21）上的甲氧基取代的查耳酮构成。此外，甲氧基查耳酮的文库已提交计算机模拟药物和药代动力学性质的预测。方法合成甲氧基查耳酮，并通过NMR光谱数据分析确定其结构。对五种念珠菌，两种革兰氏阴性菌和五种革兰氏阳性菌进行了抗菌活性评估。对于抗增殖活性，针对四种人类致瘤细胞系以及人类非致瘤性角质形成细胞评估了甲氧基查耳酮。使用Molinspiration和PreADMET工具包可预测药物相似性和药代动力学特性。结果通常，系列I的查耳酮是最有效的抗真菌，抗菌和抗增殖剂。2'，4'，5'-三甲氧基查尔酮（11）对克鲁斯假丝酵母具有有效的抗真菌活性（MIC
• Synthesis and Evaluation of Central Antinociceptive activity of Ring Substituted Chalcones; Molecular Docking Studies with Monoacylglycerol Lipase (MAGL) Enzyme
  作者：Shaheen Begum、Arifa Begum、Bharathi Koganti

  DOI：10.13005/ojc/3404024

  日期：2018.8.28

  Chalcones possess Michael acceptor property due to the presence of α,β-unsaturated enone moiety in their structure. In the present study, molecular docking was performed to predict binding affinity of ring substituted chalcones with Monoacylglycerol lipase (MAGL), a serine hydrolase enzyme which can inhibited by Michael acceptors such as maleimide derivatives. 3, 4-Dimethoxy derivative, 3h, with -44.45 kJmol-1 of interaction energy, exhibited highest binding affinity and formed Pi-Sulphur interactions with methionine-123 residue of MAGL enzyme. As MAGL is an emerging target for antinociceptive drug development, ring substituted chalcones were synthesized and evaluated for their central antinociceptive activity using tail immersion and hot plate methods. The results revealed that compound 3h, chalcone bearing methoxy groups at 3rd and 4th positions of phenyl ring exhibited good antinociceptive activity in both the models. Good correlation was observed between antinociceptive activity and binding affinity toward MAGL in case of compound 3h.

  茚酮具有Michael受体性质，因为它们的结构中存在α，β-不饱和烯酮基团。在本研究中，进行了分子对接实验，以预测环取代茚酮与单酰基甘油酶（MAGL）的结合亲和力，MAGL是一种丝氨酸水解酶酶，可以被Maleimide衍生物等Michael受体抑制。其中，具有交互作用能量-44.45 kJmol-1的3,4-二甲氧基衍生物3h表现出最高的结合亲和力，并与MAGL酶的甲硫氨酸-123残基形成Pi-硫相互作用。由于MAGL是抗疼痛药物开发的新兴靶点，因此合成了环取代茚酮，并利用尾部浸渍和热板法评估了它们的中枢抗疼痛活性。结果显示，具有在苯环的第3和第4位置带有甲氧基团的化合物3h在两种模型中均表现出良好的抗疼痛活性。在化合物3h的情况下，抗疼痛活性与其对MAGL的结合亲和力之间存在良好的相关性。