(E)-1-(2,4-difluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one

• 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-(2,4-difluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: 2',4'-difluoro-4-fluorochalcone
• 化学式: C₁₅H₉F₃O
• 分子量: 262.231
• InChiKey: QOPHENAYJAZXQV-FPYGCLRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2,4-difluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one 在 溴 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.0h， 生成 1-(2,4-difluorophenyl)-3-(p-fluorophenyl)propane-1,3-dione
  参考文献：
  名称：

  Synthesis and preliminary evaluation of difluorinated 1,3-propanediones as potential agents in the treatment of breast cancer

  摘要：

  A series of difluorinated propanediones were synthesized and evaluated for in vitro cytotoxic activity by Sulforhodamine B (SRB) assay against a panel of four human cancer cell lines. Though the compounds showed varying degrees of cytotoxicity in the tested cell lines, most marked effect was observed in breast cancer cell line (MCF7), wherein nine of the ten synthesized chalcones showed good antiproliferative activity.

  DOI：

  10.1007/s00044-011-9561-0
• 作为产物：
  描述：

  2',4'-二氟苯乙酮 、 对氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(2,4-difluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and preliminary evaluation of difluorinated 1,3-propanediones as potential agents in the treatment of breast cancer

  摘要：

  A series of difluorinated propanediones were synthesized and evaluated for in vitro cytotoxic activity by Sulforhodamine B (SRB) assay against a panel of four human cancer cell lines. Though the compounds showed varying degrees of cytotoxicity in the tested cell lines, most marked effect was observed in breast cancer cell line (MCF7), wherein nine of the ten synthesized chalcones showed good antiproliferative activity.

  DOI：

  10.1007/s00044-011-9561-0

文献信息

• Karki, Rajeshri G.; Gokhale, Vijay M.; Kharkar, Prashant S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 372 - 381
  作者：Karki, Rajeshri G.、Gokhale, Vijay M.、Kharkar, Prashant S.、Kulkarni, Vithal M.

  DOI：——

  日期：——
• Jadhav, Dhanaji H.; Ramaa, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 12, p. 2064 - 2067
  作者：Jadhav, Dhanaji H.、Ramaa

  DOI：——

  日期：——
• Synthesis and biological evaluation of α-methyl-chalcone for anti-cervical cancer activity
  作者：Bing-zhao Ren、Mourboul Ablise、Xu-chao Yang、Bo-er Liao、Zheng Yang

  DOI：10.1007/s00044-017-1891-0

  日期：2017.9

  A series of 31 chalcones were synthesized and evaluated for anti-proliferative activity against the human cervical cancer cell lines (HeLa and SiHa). Compound 19, (E)-1-(2,4-dihydroxyphenyl)-3-(4-(dimethylamino)phenyl)-2-methylprop-2-en-1-one was found to be an effective anti-proliferative agent in HeLa and SiHa cells (IC50 = 0.035 mu M). Compound 19 increased the percentage of apoptosis in a dose-dependent manner, as measured by Annexin V-FITC (fluorescein isothiocyanate)/(propidium iodide) PI staining. Molecular modeling studies of compound 19 showed that the most potent structure was docked at the yeast 20 S proteasome binding site (Protein Data Bank code-3E47) and was stabilized in the cavity by various hydrophobic and hydrogen bonding interactions.
• Synthesis and preliminary evaluation of difluorinated 1,3-propanediones as potential agents in the treatment of breast cancer
  作者：Tabreskhan Pathan、Sachin Ingale、Ashish Sharma、Rhea Mohan、C. S. Ramaa

  DOI：10.1007/s00044-011-9561-0

  日期：2012.5

  A series of difluorinated propanediones were synthesized and evaluated for in vitro cytotoxic activity by Sulforhodamine B (SRB) assay against a panel of four human cancer cell lines. Though the compounds showed varying degrees of cytotoxicity in the tested cell lines, most marked effect was observed in breast cancer cell line (MCF7), wherein nine of the ten synthesized chalcones showed good antiproliferative activity.