3-(3,4,5-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one | 215778-56-6

• 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: 3-(3,4,5-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one
• 英文别名: 1-Naphthalen-2-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 215778-56-6
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: CHKCKZJOXKQZMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one 、 胍 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以72%的产率得到4-(naphthalen-2-yl)-6-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine
  参考文献：
  名称：

  嘧啶桥联康维他汀衍生物作为潜在抗癌药的合成与生物学评价及机理研究

  摘要：

  使用MTT分析法设计，合成和评估了许多嘧啶桥联的康他汀衍生物，并评估了它们对乳腺癌（MCF-7）和肺癌（A549）细胞系的抗癌活性。大多数合成的化合物显示出良好的抗癌活性，其IC 50值在低微摩尔范围内。化合物4a和4p在该系列中最有效，对MCF7和A549癌细胞系的IC 50值分别为4.67 µM和3.38 µM和4.63 µM和3.71 µM。这些化合物的生物学评估表明，选择性癌细胞毒性（体外使用人肺癌和乳腺癌细胞系）可能是由于抗氧化剂酶的抑制导致ROS水平升高，从而触发了内在的凋亡途径。发现这些化合物对正常人原代细胞无毒。发现化合物4a是秋水仙碱的竞争性抑制剂，并且在微管蛋白结合测定中显示出与秋水仙碱相当的微管蛋白聚合抑制潜能。分子模型研究还表明，合成的化合物很好地适合秋水仙碱结合袋。

  DOI：

  10.1016/j.bioorg.2018.02.027
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(3,4,5-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one
  参考文献：
  名称：

  嘧啶桥联康维他汀衍生物作为潜在抗癌药的合成与生物学评价及机理研究

  摘要：

  使用MTT分析法设计，合成和评估了许多嘧啶桥联的康他汀衍生物，并评估了它们对乳腺癌（MCF-7）和肺癌（A549）细胞系的抗癌活性。大多数合成的化合物显示出良好的抗癌活性，其IC 50值在低微摩尔范围内。化合物4a和4p在该系列中最有效，对MCF7和A549癌细胞系的IC 50值分别为4.67 µM和3.38 µM和4.63 µM和3.71 µM。这些化合物的生物学评估表明，选择性癌细胞毒性（体外使用人肺癌和乳腺癌细胞系）可能是由于抗氧化剂酶的抑制导致ROS水平升高，从而触发了内在的凋亡途径。发现这些化合物对正常人原代细胞无毒。发现化合物4a是秋水仙碱的竞争性抑制剂，并且在微管蛋白结合测定中显示出与秋水仙碱相当的微管蛋白聚合抑制潜能。分子模型研究还表明，合成的化合物很好地适合秋水仙碱结合袋。

  DOI：

  10.1016/j.bioorg.2018.02.027

文献信息

• Synthesis and cytotoxicity study of pyrazoline derivatives of methoxy substituted naphthyl chalcones
  作者：K. R. Ethiraj、P. Nithya、V. Krishnakumar、A. Jesil Mathew、F. Nawaz Khan

  DOI：10.1007/s11164-012-0718-3

  日期：2013.4

  2-Acetyl naphthalene reacts with various methoxy substituted benzaldehyde in the presence of 10 % sodium hydroxide solution giving functionalized chalcones. The synthesized chalcones when further reacted with hydrazine hydrate in the presence of acetic acid afforded N-acetyl pyrazolines. All the synthesized products were confirmed by various spectral data such as FTIR, 1H NMR, 13C NMR, and HRMS studies. All the synthesized compounds were screened for cytotoxicity against various cell lines.

  2-乙酰萘与不同的甲氧基取代苯甲醛在10%氢氧化钠溶液的存在下反应，生成功能化的查尔酮。当合成的查尔酮进一步与水合肼在醋酸的存在下反应时，得到N-乙酰吡唑啉。所有合成产物通过FTIR、1H NMR、13C NMR和HRMS等各类谱学数据进行确认。所有合成的化合物均进行了对各种细胞系的细胞毒性筛选。
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .
• Synthesis of Methoxy-substituted Chalcones and<i>in vitro</i>Evaluation of their Anticancer Potential
  作者：Kannatt Radhakrishnan Ethiraj、Jesil Mathew Aranjani、Fazlur-Rahman Nawaz Khan

  DOI：10.1111/cbdd.12184

  日期：2013.12

  Methoxy‐substituted chalcones, 3 were obtained using simple, efficient method from 2‐naphtylethanone, 1 and aromatic aldehydes, 2. The in vitro cytotoxicity activities of the chalcones against a panel of three human cancer cell lines were explored. The tested compounds were found to possess significant cytotoxic activity. The DNA strand break and damage was quantified through alkaline comet assay, flow cytometric analysis, and chromatin condensation studies, which revealed the apoptotic nature of the compounds. Compound 3c, (3‐(3,4,5‐trimethoxyphenyl)‐1‐(2‐naphthyl) prop‐2‐en‐1‐one) showed highest cytotoxicity of 0.019 μm against HeLa, 0.020 μm against HCT15 and 0.022 μm against A549. Compound 3e, (3‐(3,5‐dimethoxyphenyl)‐1‐(2‐naphthyl) prop‐2‐en‐1‐one) showed better IC50 values against all the three cell lines employed for the study.
• Halogenated naphthochalcones and structurally related naphthopyrazolines with antitumor activity
  作者：Florian Schmitt、Heidrun Draut、Bernhard Biersack、Rainer Schobert

  DOI：10.1016/j.bmcl.2016.09.076

  日期：2016.11

  Three 3-(3-halo-4,5-dimethoxypheny1)-1-(2-naphthyl)prop-2-en-1 -ones 1 and three structurally related 2-pyrazolines 2 were prepared and assessed in vitro for anticancer activity. The chalcones 1 were antiproliferative with low double-digit micromolar IC50 values against six tumor cell lines whereas the pyrazolines 2 showed low single-digit micromolar IC50) values against this panel. The pyrazolines inhibited ATP binding cassette efflux transporters of types P-gp and BCRP while the chalcones inhibited selectively BCRP. All test compounds induced an accumulation of HT-29 colon carcinoma cells in the G2/M phase of the cell cycle and they interfered with the microtubule and F-actin dynamics, but only the chalcones induced apoptosis in 518A2 melanoma cells after 24 h. (C) 2016 Elsevier Ltd. All rights reserved.