(E)-3-(4-methoxyphenyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

• 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-(4-methoxyphenyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 4,2’,3’,4’-tetramethoxychalcone；4.2'.3'.4'-tetramethoxy-trans-chalcone；4.2'.3'.4'-Tetramethoxy-trans-chalkon
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: LLOMFMKNJPVRPK-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-3-(4-methoxyphenyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 在 乙醇 、 溶剂黄146 、 锌 作用下， 生成 3,4-bis-(4-methoxy-phenyl)-1,6-bis-(2,3,4-trimethoxy-phenyl)-hexane-1,6-dione
  参考文献：
  名称：

  656.单宁的结构。第一部分：粉笔粉的还原

  摘要：

  DOI：

  10.1039/jr9500003367
• 作为产物：
  描述：

  2',3',4'-三甲氧基苯乙酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以73%的产率得到(E)-3-(4-methoxyphenyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of Oxygenated Chalcones with Anti-Staphylococcal Activity

  摘要：

  革兰氏阳性菌是住院患者皮肤感染的最常见原因，其中葡萄球菌 金黄色葡萄球菌是导致死亡的主要病原体。合成了一系列多氧化查耳酮 并测定抗葡萄球菌活性。羟基化查耳酮在抑制微生物方面更有效 比甲氧基化类似物生长更快。化合物3',5',4-三羟基查耳酮是其中最有前途的化合物 经评估，显示出比苯唑西林更广泛的抗菌谱，对多重耐药菌的 MIC 为 64 µg/ml 金黄色葡萄球菌的医院临床菌株。

  DOI：

  10.2174/1570180810666131125221032

文献信息

• Antimalarial Alkoxylated and Hydroxylated Chalones:  Structure−Activity Relationship Analysis
  作者：Mei Liu、Prapon Wilairat、Mei-Lin Go

  DOI：10.1021/jm0101747

  日期：2001.12.1

  among the active compounds. Hydroxylated chalcones were less active than the corresponding alkoxylated analogues. When evaluated in vivo, 8 and 208 were comparable to chloroquine in extending the lifespan of infected mice. Multivariate data analysis showed that in vitro activity was mainly determined by the properties of ring B. Quantitative structure-activity relationship models with satisfactory predictive

  合成在环B上具有2'，3'，4'-三甲氧基，2'，4'-二甲氧基，4'-甲氧基，4'-乙氧基，2'，4'-二羟基和4'-羟基的邻苯二甲酰并在[3H]次黄嘌呤摄取测定中针对恶性疟原虫（K1）进行了体外评估。另一个环A是具有不同亲脂性的给电子或吸电子取代基的喹啉，吡啶，萘或苯环。三甲氧基6和27，二甲氧基7，8，29和甲氧基31类似物具有良好的体外活性（IC（50）<5 microM）。在活性化合物中很好地代表了3-喹啉基环A衍生物。羟基查耳酮的活性低于相应的烷氧基化类似物。在体内评估时，8和208在延长被感染小鼠的寿命方面与氯喹相当。多变量数据分析表明，体外活性主要取决于环B的特性。使用对潜在结构的投影，获得了各种B环查耳酮具有令人满意的预测能力的定量构效关系模型。提出了一个具有良好可预测性的模型，用于19个活动查尔肯。尺寸和疏水性被确定为关键参数。
• Synthesis of Oxygenated Chalcones with Anti-Staphylococcal Activity
  作者：Luciana Dalla-Vechia、Cíntia Kiekow、Ivana Leal、Katia Santos、Simone Gnoatto、Hugo Verli、Rodrigo Souza、Grace Gosmann

  DOI：10.2174/1570180810666131125221032

  日期：2013.11.25

  Gram-positive bacteria are the most common cause of skin infection in hospitalized patients, with Staphylococcus aureus being the principal pathogen responsible for deaths. A series of poly-oxygenated chalcones was synthesized and assayed for anti-staphylococcal activity. Hydroxylated chalcones were more effective in the inhibition of microbial growth than methoxylated analogues. The compound 3’,5’,4-trihydroxychalcone is the most promising compound among those evaluated, showing a much broader antimicrobial spectrum than oxacillin and a MIC of 64 µg/ml to a multidrug- resistant hospital clinical strain of S. aureus.

  革兰氏阳性菌是住院患者皮肤感染的最常见原因，其中葡萄球菌 金黄色葡萄球菌是导致死亡的主要病原体。合成了一系列多氧化查耳酮 并测定抗葡萄球菌活性。羟基化查耳酮在抑制微生物方面更有效 比甲氧基化类似物生长更快。化合物3',5',4-三羟基查耳酮是其中最有前途的化合物 经评估，显示出比苯唑西林更广泛的抗菌谱，对多重耐药菌的 MIC 为 64 µg/ml 金黄色葡萄球菌的医院临床菌株。
• Kuroda; Matsukuma, Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1932, vol. 18, p. 51,58
  作者：Kuroda、Matsukuma

  DOI：——

  日期：——
• 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.
• 58. The constitution of tannins. Part I. Reduction products of chalkones and the synthesis of a typical phlobatannin
  作者：Alfred Russell

  DOI：10.1039/jr9340000218

  日期：——