1-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one | 500308-92-9

• 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: 1-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
• 英文别名: 3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-one
• CAS: 500308-92-9
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: FARTWAUUUXFSFV-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  480.4±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one 在 sodium tetrahydroborate 作用下， 生成 3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-ol
  参考文献：
  名称：

  Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents

  摘要：

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。

  DOI：

  10.1039/c4ra03823a
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 palladium on activated charcoal 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 1-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents

  摘要：

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。

  DOI：

  10.1039/c4ra03823a

文献信息

• Identification of chalcone analogues as anti-inflammatory agents through the regulation of NF-κB and JNK activation
  作者：Die Zhang、Wenping Wang、Huiping Ou、Jinhua Ning、Yingxun Zhou、Jin Ke、Anguo Hou、Linyun Chen、Peng Li、Yunshu Ma、Wen Bin Jin

  DOI：10.1039/d4md00011k

  日期：——

  To develop new anti-inflammatory agents with improved pharmaceutical profiles, a series of chalcone analogues were designed and synthesized. In vitro anti-inflammatory activity of these compounds was evaluated by screening their inhibitory effects on NO production in RAW264.7 cell lines. The most promising compounds 3h and 3l were selected for further investigation by assessment of their dose-dependent

  为了开发具有改进药物特性的新型抗炎剂，设计并合成了一系列查尔酮类似物。通过筛选这些化合物对 RAW264.7 细胞系中 NO 产生的抑制作用来评估这些化合物的体外抗炎活性。通过评估其对细胞因子（如 TNF-α、IL-1β、IL-6 和 PGE2 释放）的剂量依赖性抑制活性，选择最有前途的化合物3h和3l进行进一步研究。进一步研究还表明3h和3l可通过NF-κB/JNK信号通路显着抑制iNOS和COX-2的表达。此外，化合物3h和3l还可以显着抑制炎症相关基因的mRNA表达。同时， 3小时也可以下调ROS的产生。进行对接模拟以将化合物3h和3l定位到 iNOS 结合位点以预测可能的结合模式。总之，通过计算机快速预测获得的这一系列具有合理药物相似性的查耳酮类似物可以用作有前途的先导候选物。
• Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
  作者：Sylvie Ducki、David Rennison、Meiko Woo、Alexander Kendall、Jérémie Fournier Dit Chabert、Alan T. McGown、Nicholas J. Lawrence

  DOI：10.1016/j.bmc.2009.09.039

  日期：2009.11

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Discovery of Loureirin analogues with colorectal cancer suppressive activity via regulating cell cycle and Fas death receptor
  作者：Peng Li、Xiangjuan Tian、Die Zhang、Huiping Ou、Qiufeng Huang、Wenbin Jin、Ran Liu

  DOI：10.1186/s40360-024-00758-2

  日期：——

  Chalcones and dihydrochalcones (DHCs) are important bioactive natural products (BNPs) isolated from traditional Chinese medicine. In this study, 13 chalcones were designed with the inspiration of Loureirin, a DHC extracted from Resina Draconis, and synthesized by classical Claisen-Schmidt reactions. Afterwards the reduction reactions were carried out to obtain the corresponding DHCs. Cytotoxicity assay indicated chalcones and DHCs possessed selective cytotoxicity against colorectal cancer (CRC) cells. The preliminary structure-activity relationships (SAR) of these compounds suggested the α, β-unsaturated ketone of the chalcones were crucial for the anticancer activity. Interestingly, compounds 3d and 4c exhibited selective anticancer activity against CRC cell line HCT116 with IC50s of 8.4 and 17.9 μM but not normal cell. Moreover, 4c could also inhibit the migration and invasion of CRC cells. Mechanism investigations showed 4c could induce cell cycle G2/M arrest by regulating cell cycle-associated proteins and could also up-regulate Fas cell surface death receptor. The virtual docking further pointed out that compounds 3d and 4c could nicely bind to the Fas/FADD death domain complex (ID: 3EZQ). Furthermore, silencing of Fas significantly enhanced the proliferation of CRC cells and attenuated the cytotoxicity induced by 4c. These results suggested 4c exerted its anticancer activity possibly regulating cell cycle and Fas death receptor. In summary, this study investigated the anticancer activity and mechanism of Loureirin analogues in CRC, suggesting these compounds may warrant further investigation as promising anticancer drug candidates for the treatment of CRC.