(E)-2-benzylsulfonyl-1-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one | 1370519-64-4

• 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: (E)-2-benzylsulfonyl-1-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 1370519-64-4
• 化学式: C₂₄H₁₉F₃O₄S
• 分子量: 460.474
• InChiKey: ZOLDITRQRUPJHN-PXLXIMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酮 在 ammonium acetate 、 双氧水 、 溴 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成 (E)-2-benzylsulfonyl-1-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel (E)-α-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors

  摘要：

  Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAF(V600E). It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF(V600E) inhibitor. Based on its structure, a series of novel (E)-alpha-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC50 value of 0.17 mu M for BRAF(V600E) and GI(50) value of 0.52 mu M for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.007

文献信息

• Design, synthesis and biological evaluation of novel (E)-α-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors
  作者：Qing-Shan Li、Cui-Yun Li、Xiang Lu、Hui Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2012.02.007

  日期：2012.4

  Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAF(V600E). It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF(V600E) inhibitor. Based on its structure, a series of novel (E)-alpha-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC50 value of 0.17 mu M for BRAF(V600E) and GI(50) value of 0.52 mu M for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF. (C) 2012 Elsevier Masson SAS. All rights reserved.