(E)-1-(4-methoxyphenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one | 131887-83-7

• 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-(4-ethoxyphenyl)prop-2-en-1-one
• 英文别名: 4-ethoxy-4'-methoxychalcone；(E)-3-(4-ethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one；4-ethoxy-4'-methoxy-trans-chalcone；4-Aethoxy-4'-methoxy-trans-chalkon；3-(4-ethoxyphenyl)-1-(4-methoxyphenyl)-2-propene-1-one；trans-4-Ethoxy-4'-methoxychalcone
• CAS: 131887-83-7
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: OCJRMZSSQYAGCZ-AWNIVKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙氧基苯甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-1-(4-methoxyphenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcones and Bis-Chalcones Analogs as DPPH and ABTS Radical Scavengers

  摘要：

  背景：许多合成支架物以及天然产物被确定为有效的抗氧化剂。本研究涉及对不同取代、具有药用特性的化合物类别“查尔酮和双查尔酮”进行抗氧化潜力评估。 方法：对一系列合成查尔酮1-13和双查尔酮14-18进行体外自由基清除活性测试。 结果：所有分子1-18在IC50范围内显示出明显的2,2-二苯基-1-苯基-亚硝基肼（DPPH）和2,2'-联苯二(3-乙基苯并噻唑啉-6-磺酸)（ABTS）自由基清除潜力，分别为0.58 ± 0.14 - 1.72 ± 0.03和0.49 ± 0.3 - 1.48 ± 0.06 μM。抗坏血酸（DPPH和ABTS的IC50分别为0.5 ± 0.1和0.46 ± 0.17 μM）被用作标准自由基清除剂。 结论：结构活性关系（SAR）显示了各种基团，包括-SMe和-OMe在清除活性中的积极参与。

  DOI：

  10.2174/1570180817999201001155032

文献信息

• Synthesis and Cytotoxic Evaluation of Alkoxylated Chalcones
  作者：Xiao-Guang Bai、Chang-Liang Xu、Shuang-Shuang Zhao、Hong-Wei He、Yu-Cheng Wang、Ju-Xian Wang

  DOI：10.3390/molecules191117256

  日期：——

  A series of chalcones a1–20 bearing a 4-OMe groups on the A-ring were initially synthesized and their anticancer activities towards HepG2 cells evaluated. Subsequently, a series of chalcones b1–42 bearing methoxy groups at the 2' and 6'-positions of the B-ring were synthesized and their anticancer activities towards five human cancer cell lines (HepG2, HeLa, MCF-7, A549 and SW1990) and two non-tumoral human cell lines evaluated. The results showed that six compounds (b6, b8, b11, b16, b18, b22, b23 and b29) displayed promising activities, with compounds b22 and b29 in particular showing higher levels of activity than etoposide against all five cancer cell lines. Compound b29 showed a promising SI value compared with both HMLE and L02 (2.1–6.5 fold in HMLE and > 33 > 103.1 fold in L02, respectively).

  一系列在A环上带有4-OMe基团查尔酮a1-20被合成，并评估了它们对HepG2细胞的抗癌活性。随后，合成了一系列在B环的2'和6'-位置带有甲氧基的查尔酮b1-42，并评估了它们对五种人癌细胞系（HepG2、HeLa、MCF-7、A549和SW1990）和两种非瘤人细胞系的抗癌活性。结果显示，六个化合物（b6、b8、b11、b16、b18、b22、b23和b29）显示出有望的活性，特别是化合物b22和b29在所有五种癌细胞系中显示出比依托泊苷更高的活性水平。与HMLE和L02相比，化合物b29显示出有希望的SI值（分别是HMLE的2.1-6.5倍，L02的>103.1倍）。
• Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues
  作者：Monika Stompor、Barbara Żarowska

  DOI：10.3390/molecules21050608

  日期：——

  which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4'-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4'-methoxychalcones or its replacement by a halogen atom (-Cl, -Br), nitro group (-NO₂), ethoxy group (-OCH₂CH₃), or aliphatic substituent (-CH₃, -CH₂CH₃) resulted in the loss of antimicrobial activity towards

  这项研究的目的是评估xanthohumol 1（一种在啤酒花中发现的类黄酮化合物）的结构类似物的抗菌活性。应用了使用滤纸盘的琼脂扩散方法。对革兰氏阳性（金黄色葡萄球菌）和革兰氏阴性（大肠埃希氏菌）细菌，真菌（Alternaria sp。）和酵母（Rhodotorula rubra，白色念珠菌）的选定菌株进行的生物学测试显示，至少具有一个羟基的化合物他们所有人都在C-4位置表现出良好的表现。我们的研究表明，金黄色葡萄球菌对查耳酮比对杂环C封闭的异构体（黄酮）更敏感。R. rubra菌株仅对一种化合物中等敏感：4-羟基-4'-甲氧基查耳酮8。4′-甲氧基查尔酮的B环中羟基的丢失或被卤素原子（-Cl，-Br），硝基（-NO 2），乙氧基（-OCH 2 CH 3）或脂族取代基（-CH 3）取代，-CH 2 CH 3）导致对红曲霉酵母和金黄色葡萄球菌的抗菌活性丧失。Xanthohumol 1，柚皮苷
• Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia
  作者：Julio Montes-Avila、Sylvia P. Díaz-Camacho、Josefina Sicairos-Félix、Francisco Delgado-Vargas、I.A. Rivero

  DOI：10.1016/j.bmc.2009.02.052

  日期：2009.9

  A library of 25-membered chalcones was prepared by parallel synthesis. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Several chalcones showed in vitro antiparasitic activity against Giardia lamblia. The highest activity observed for the IC50 values were 12.72, 15.05 and 15.31 mu g/mL, respectively; these are potential leads for the development of antigiardial compounds. (C) 2009 Elsevier Ltd. All rights reserved.
• Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
  作者：Adebayo Tajudeen Bale、Khalid Mohammed Khan、Uzma Salar、Sridevi Chigurupati、Tolulope Fasina、Farman Ali、Kanwal、Abdul Wadood、Muhammad Taha、Sitansu Sekhar Nanda、Mehreen Ghufran、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.05.003

  日期：2018.9

  Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible alpha-amylase inhibitory activity. So, the current study is based on the evaluation of this class for the identification of new leads as alpha-amylase inhibitors. For that purpose, a library of substituted chalcones 1-13 and bis-chalcones 14-18 were synthesized and characterized by spectroscopic techniques EI-MS and H-1 NMR. CHN analysis was carried out and found in agreement with the calculated values. All compounds were evaluated for in vitro alpha-amylase inhibitory activity and demonstrated good activities in the range of IC50 = 1.25 +/- 1.05-2.40 +/- 0.09 mu M as compared to the standard acarbose (IC50 = 1.04 +/- 0.3 mu M). Limited structure-activity relationship (SAR) was established by considering the effect of different groups attached to aryl rings on varying inhibitory activity. SMe group in chalcones and OMe group in bis-chalcones were found more influential on the activity than other groups. However, in order to predict the involvement of different groups in the binding interactions with the active site of alpha-amylase enzyme, in silico studies were also conducted.
• A Study of the Direction of Enolization of p-Methoxy-p'-bromodibenzoylmethane and p-Methoxy-p'-ethoxydibenzoylmethane
  作者：R. Percy Barnes、Thomas C. Goodwin、Thomas W. Cotten

  DOI：10.1021/ja01204a059

  日期：1947.12

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