(Z)-5-(4-bromobenzylidene)-3-(4-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one | 1448459-19-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-5-(4-bromobenzylidene)-3-(4-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one
• 英文别名: (5Z)-5-[(4-bromophenyl)methylidene]-3-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)furan-2-one
• CAS: 1448459-19-5
• 化学式: C₂₄H₁₆BrFO₄S
• 分子量: 499.357
• InChiKey: YGDWTMHUZMDJIU-STZFKDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 硫酸 、 氢溴酸 、 双氧水 、 sodium carbonate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.58h， 生成 (Z)-5-(4-bromobenzylidene)-3-(4-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one
  参考文献：
  名称：

  Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

  摘要：

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.062

文献信息

• Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones
  作者：Gai-Zhi Liu、Hai-Wei Xu、Peng Wang、Zong-Tao Lin、Ying-Chao Duan、Jia-Xin Zheng、Hong-Min Liu

  DOI：10.1016/j.ejmech.2013.04.062

  日期：2013.7

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.