(E)-1-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl) prop-2-en-1-one | 177984-96-2

• 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-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl) prop-2-en-1-one
• 英文别名: 1-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• CAS: 177984-96-2
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: KCTNGNPVURILGU-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  458.7±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl) prop-2-en-1-one 、 溶剂黄146 在 一水合肼 作用下， 反应 2.0h， 生成 1-(3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-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：

  对氯苯乙酮 、 香草醛 以79%的产率得到(E)-1-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl) prop-2-en-1-one
  参考文献：
  名称：

  Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical

  摘要：

  通过适当的苯乙酮与芳基化合物之间的克莱森-施密特缩合反应，合成了 16 种纯度足够高的羟基查耳酮。 通过适当的苯乙酮和芳基醛之间的克莱森-施密特缩合反应，合成了十六种纯度足够高的羟基查耳酮。 醛缩合合成了十六种纯度足够高的羟基查耳酮。对所有化合物清除稳定的游离 2,2- 二苯基-1-丙酮的能力进行了评估。 稳定的游离 2,2-二苯基-1-苦基肼（DPPH）自由基的能力进行了评估。观察到重要的 结构与活性的关系，这大大有助于 的知识。相关的 理论参数，试图理解和解释所获得的实验结果。 实验结果。

  DOI：

  10.2298/jsc100517043t

文献信息

• Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical
  作者：Iva Todorova、Daniela Batovska、Bistra Stamboliyska、Stoyan Parushev

  DOI：10.2298/jsc100517043t

  日期：——

  Sixteen hydroxychalcones were synthesized in sufficient purity by the Claisen-Schmidt condensation between appropriate acetophenones and aryl aldehydes. All the compounds were evaluated for their ability to scavenge the stable free 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Important structure-activity relationships were observed that strongly contribute to the knowledge for the design of DPPH radical scavenging chalcones. Relevant theoretical parameters were computed in an attempt to understand and explain the obtained experimental results.

  通过适当的苯乙酮与芳基化合物之间的克莱森-施密特缩合反应，合成了 16 种纯度足够高的羟基查耳酮。 通过适当的苯乙酮和芳基醛之间的克莱森-施密特缩合反应，合成了十六种纯度足够高的羟基查耳酮。 醛缩合合成了十六种纯度足够高的羟基查耳酮。对所有化合物清除稳定的游离 2,2- 二苯基-1-丙酮的能力进行了评估。 稳定的游离 2,2-二苯基-1-苦基肼（DPPH）自由基的能力进行了评估。观察到重要的 结构与活性的关系，这大大有助于 的知识。相关的 理论参数，试图理解和解释所获得的实验结果。 实验结果。
• Zhao, Fei; Zhao, Qing-Jie; Zhang, Da-Zhi, Asian Journal of Chemistry, 2011, vol. 23, # 12, p. 5339 - 5342
  作者：Zhao, Fei、Zhao, Qing-Jie、Zhang, Da-Zhi、Jin, Yong-Sheng、Zhang, Wei

  DOI：——

  日期：——
• Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline—isatin hybrids
  作者：Manmohan Sharma、Sahil Sharma、Abhishek Buddhiraja、A. K. Saxena、Kunal Nepali、P. M. S. Bedi

  DOI：10.1007/s00044-014-1001-5

  日期：2014.10

  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..