1-(3,4,5-trimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one | 1159190-79-0

• 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: 1-(3,4,5-trimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• 英文别名: 4-hydroxy-3,3',4',5'-tetramethoxychalcone；3-(4-hydroxy-3-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1159190-79-0
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: NJOQNOIPLGPXPO-UHFFFAOYSA-N

物化性质

• 沸点：
  529.9±50.0 °C(predicted)
• 密度：
  1.211±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 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：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 一水合肼 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1-(5-(4-((1-(2-(2,3-dioxoindolyl)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)-4,5-dihydro-3-(3,4,5-trimethoxyphenyl)pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline—isatin hybrids

  摘要：

  Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Miapaca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetyl-pyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 mu M against HeLa Cell line..

  DOI：

  10.1007/s00044-014-1001-5
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 香草醛 在 sodium hydroxide 作用下， 反应 2.0h， 生成 1-(3,4,5-trimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  设计，合成和筛选作为潜在细胞毒性分子的4,6-二芳基吡啶和嘧啶衍生物。

  摘要：

  设计并合成了一系列新的吡啶和嘧啶衍生物，作为潜在的抗肿瘤分子。受测试的化合物显示出对HL-60细胞系的有希望的体外细胞毒性活性，这是因为以下8种化合物：4、6、11、13、14、15、18和21在亚微摩尔浓度下均表现出高于康普他汀A4（CA -4）。化合物21对HL-60细胞的细胞毒活性比CA-4强5倍。DNA流式细胞术细胞周期分析和对HL-60细胞的膜联蛋白V分析表明，化合物4、18和21表现出有效的细胞生长抑制作用，细胞周期阻滞在G2 / M期和促凋亡诱导活性。β-微管蛋白聚合对HL-60细胞的抑制百分比测定表明，所测试化合物的抗肿瘤活性似乎与其抑制β-微管蛋白聚合的能力密切相关。此外，化合物21的酶联免疫吸附法（ELlSA）测量显示出通过上调p53，Bax / Bcl-2比值和caspase-3蛋白的显着上调，同时下调survivin蛋白的水平，诱导了细胞凋亡。

  DOI：

  10.1248/cpb.c18-00269

文献信息

• Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted
  作者：Daniela Batovska、Stoyan Parushev、Bistra Stamboliyska、Iva Tsvetkova、Mariana Ninova、Hristo Najdenski

  DOI：10.1016/j.ejmech.2008.05.010

  日期：2009.5

  A large series of chalcones were synthesized and studied against Staphylococcus aureus and Escherichia coli. Chalcones were either unsubstituted in ring A or possessed 4-chloro or 3',4',5'-trimethoxy groups. Their other ring B was variously substituted. It was found that the antistaphylococcal activity of chalcones was related to the energy difference between the two highest occupied molecular orbitals (HOMO and HOMO-1). Presence of hydroxyl group in ring B was not a determinant factor for the anti-staphylococcal activity, but the lipophilicity of ring A of the hydroxyl chalcones was of importance. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Identification of 3′,4′,5′-trimethoxychalcone analogues as potent inhibitors of Helicobacter pylori-induced inflammation in human gastric epithelial cells
  作者：Chih-Ho Lai、Yerra Koteswara Rao、Shih-Hua Fang、Yu-Ting Sing、Yew-Min Tzeng

  DOI：10.1016/j.bmcl.2010.07.094

  日期：2010.9

  Efforts to identify potent small molecule inhibitors of Helicobacter pylori led to the evaluation of 23 3',4',5'-trimethoxychalcone analogues. Some of the compounds displayed potent antibacterial activity against H. pylori. Three most active and selective compounds 1, 7, and 13 also showed the bactericide activity against the reference as well as multidrug-resistant strains of H. pylori. Additionally, the aforementioned three compounds potentially inhibited the H. pylori adhesion and invasion to human gastric epithelial (AGS) cells. Furthermore, these selective compounds inhibited the H. pylori-induced gastric inflammation by reduced inflammatory mediator's nuclear factor kappa B activation, and the secretion of interleukin-8. (c) 2010 Elsevier Ltd. All rights reserved.
• Antimicrobial, Anti-Inflammatory and Antioxidant Activities of Polyoxygenated Chalcones
  作者：Yesseny Vásquez-Martínez、Mauricio Osorio、Diego San Martín、Marcela Carvajal、Alejandra Vergara、Elizabeth Sanchez、Marcela Raimondi、Susana Zacchino、Carolina Mascayano、Claudia Torrent、Francisco Cabezas、Sophia Mejias、Margarita Montoya、Marcelo Cortez-San Martín

  DOI：10.21577/0103-5053.20180177

  日期：——

  It was synthesized nine polyoxygenated chalcones with a potential and safe use as antioxidant, antimicrobial and anti-inflammatory therapies. Chalcones obtained by Claisen-Schmidt condensation were studied as antioxidant, inhibitors of human 5-lipoxygenase, antifungal, antibacterial and antibiotic resistance modifiers. Two chalcones with catecholic moieties were able to strongly decrease the minimum inhibitory concentration (MIC) of methicillin against methicillin-resistant Staphylococcus aureus, increase the antiradical activity and significantly inhibit the human 5-lipoxygenase. Only one of these chalcones was active synergistically with methicillin. Chalcones with methoxyl substituents at different positions displayed the best activities against Cryptococcus neoformans. Only one chalcone showed good activity against the plant pathogenic bacteria Pseudomonas syringae whose half maximal inhibitory concentration (IC50) value (2.5 mu g mL(-1)) was similar to that observed with the antibiotic streptomycin (2.9 mu g mL(-1)). These simple chalcones have safe potential uses in antioxidant, antimicrobial and anti-inflammatory therapies.
• 3′,4′,5′-trimethoxy- and 3,4-dimethoxychalcones targeting A549 cells: Synthesis, cytotoxic activity, and molecular docking
  作者：Ade Danova、Duy Vu Nguyen、Riho Toyoda、Panupong Mahalapbutr、Thanyada Rungrotmongkol、Piyanuch Wonganan、Warinthorn Chavasiri

  DOI：10.1016/j.molstruc.2022.134572

  日期：2023.3