3-(2,3,4-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one | 556784-88-4

• 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-(2,3,4-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one
• 英文别名: 1-naphthalen-2-yl-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• CAS: 556784-88-4
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: IYBOMVIDVNDNHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2,3,4-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one 、 溶剂黄146 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以59%的产率得到1-[4,5-dihydro-5-(2,3,4-trimethoxyphenyl)-3-(naphth-2-yl)-1H-pyrazol-1-yl]ethanone
  参考文献：
  名称：

  Synthesis and cytotoxicity study of pyrazoline derivatives of methoxy substituted naphthyl chalcones

  摘要：

  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。

  DOI：

  10.1007/s11164-012-0718-3
• 作为产物：
  描述：

  2-萘乙酮 、 2,3,4-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-(2,3,4-trimethoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and cytotoxicity study of pyrazoline derivatives of methoxy substituted naphthyl chalcones

  摘要：

  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。

  DOI：

  10.1007/s11164-012-0718-3

文献信息

• 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.