(E)-3-(3"-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one | 934022-25-0

• 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-(3"-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one
• 英文别名: (E)-3-(3-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl) prop-2-en-1-one；(E)-3-(3-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；3,3',4',5'-tetramethoxychalcone
• CAS: 934022-25-0
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: JMTGUGXQVBQMIV-CMDGGOBGSA-N

物化性质

• 熔点：
  65-67 °C(Solv: methanol (67-56-1))
• 沸点：
  499.8±45.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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-(3"-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one 在 双氧水 、 potassium carbonate 、 对甲苯磺酸 、 一水合肼 作用下， 以 甲醇 、 水 、 xylene 为溶剂， 反应 6.0h， 生成 5-(3-Methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis and cytotoxicity of epoxide and pyrazole analogs of the combretastatins

  摘要：

  Twenty-six epoxide and corresponding pyrazole derivatives, of the structurally related chalcones and combretastatin A-4 (CA-4), were synthesized and tested for in vitro cytotoxicity. These molecules were synthesized by epoxidation of the relevant chalcones, followed by reaction with hydrazine. The structures of epoxides 3 and 7, and pyrazole 17, were confirmed by X-ray diffraction studies. The relatively coplanar conformation of a 3',3",4',4",5',5"-hexamethoxypyrazole 17 was in good agreement with the shape for 3',3",4',4",5'-pentamethoxypyrazole 16, which was determined from molecular mechanics optimization. In vitro cytotoxicity of each class of compounds was obtained using a 72 h continuous exposure MTT assay against two murine cancer cell lines; B16 melanoma and L1210 leukemia. The effect of substitution in the A-ring is addressed: three methoxy groups versus two, generally increased cytotoxicity across both cell lines. In the majority of cases, the pyrazoles are generally more active than the epoxides, with the most active, 5-(3"-amino-4"-methoxyphenyl)-3-(3',4',5'-trimethoxyphenyl)pyrazole 21, possessing an IC50 value of 5 and 2.4 mu M (B16 and L1210, respectively). Due to their planar conformations, the pyrazoles are typically less active than the corresponding chalcones, which adopt angular conformations similar to CA-4. B-ring modifications confirmed that in general the amino compounds are more active than the corresponding nitro compounds. Varying the number and orientation of methoxy groups on the A-ring did not produce any significant differences in toxicity in the cell lines studied. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.028
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 3-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以78%的产率得到(E)-3-(3"-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  研究一系列合成查耳酮对酵母白色念珠菌的取代基作用。

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2006.08.012

文献信息

• Design, Synthesis and Biological Evaluation of Dimethyl Cardamonin (DMC) Derivatives as P-glycoprotein-mediated Multidrug Resistance Reversal Agents
  作者：Ximeng Shi、Yuyu Zhao、Licheng Zhou、Huanhuan Yin、Jianwen Liu、Lei Ma

  DOI：10.2174/1570180817999200531162015

  日期：2020.10.12

  Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting Pgp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin

  背景：过去十年来，P-糖蛋白（P-gp）被认为是肿瘤细胞多药耐药性（MDR）的重要因素，可以通过抑制Pgp逆转MDR来解决。因此，开发P-gp抑制剂是一种有效的策略。 目的：本研究在二甲基小豆蔻苷（DMC）的基础上，通过生物等位线设计进行了一系列衍生物的合成。随后，我们评估了它们作为潜在的P-糖蛋白（P-gp）介导的多药耐药性（MDR）药物的逆转活性。 方法：在40％KOH存在下，通过Claisen-Schmidt反应，由苯乙酮和相应的苯甲醛合成二甲基豆蔻苷衍生物。用MTT评估它们的体外细胞毒性和逆转活性。此外，通过阿霉素（DOX）积累，蛋白质印迹和伤口愈合分析对化合物B4进行了深入评估。 结果与讨论：结果表明，化合物B2，B4和B6具有MDR反向剂的效力，而固有的细胞毒性很小。同时，这些化合物还显示出抑制MCF-7和MCF-7 / DOX细胞迁移的能力。此外，选择了最多的化合物B4进行进一步的研究，它促进了DOX在MCF-7
• Synthesis and biological evaluation of 3′,4′,5′-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation
  作者：Yerra Koteswara Rao、Shih-Hua Fang、Yew-Min Tzeng

  DOI：10.1016/j.bmc.2009.10.022

  日期：2009.12

  anti-proliferative compound in the series with IC50 values of 1.8 and 2.2 μM toward liver cancer Hep G2 and colon cancer Colon 205 cell lines, respectively. 2,3,3′,4′,5′-Pentamethoxychalcone (1), 3,3′,4,4′,5,5′-hexamethoxychalcone (3), 2,3′,4,4′,5,5′-hexamethoxychalcone (5), 2-hydroxy-3,3′,4′,5′-tetramethoxychalcone (10), 11 and 14 showed significant anti-proliferation actions in Hep G2 and Colon 205

  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
• 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。
• The synthesis and Angiotensin Converting Enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives
  作者：Marco Bonesi、Monica R. Loizzo、Giancarlo A. Statti、Sylvie Michel、François Tillequin、Francesco Menichini

  DOI：10.1016/j.bmcl.2010.01.113

  日期：2010.3

  A series of chalcones (1-9) and pyrazoles (10-18) was prepared to investigate their potential activity as Angiotensin I-Converting Enzyme (ACE) inhibitors. Their structures were verified by elemental analysis, UV, IR, MS, H-1 NMR, C-13 NMR, and 2D NMR experiments. Among tested compounds, chalcone 7 exerted the highest activity with an IC50 value of 0.219 mM, while the most potent pyrazole was 15 (IC50 value of 0.213 mM). (C) 2010 Elsevier Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of thiophene analogues of chalcones
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Olga Cruz-Lopez、Delia Preti、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Nicola Zonta、Jan Balzarini、Andrea Brancale、Taradas Sarkar、Ernest Hamel

  DOI：10.1016/j.bmc.2008.04.026

  日期：2008.5

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.