N-[4-(2-bromoacetyl)phenyl]-4-fluorobenzenesulfonamide | 610259-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[4-(2-bromoacetyl)phenyl]-4-fluorobenzenesulfonamide
• CAS: 610259-64-8
• 化学式: C₁₄H₁₁BrFNO₃S
• 分子量: 372.215
• InChiKey: RMNBFYPUOKGJSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(2-bromoacetyl)phenyl]-4-fluorobenzenesulfonamide 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 S-[2-[4-[(4-fluorophenyl)sulfonylamino]phenyl]-2-oxoethyl] ethanethioate
  参考文献：
  名称：

  α-Mercaptoketone based histone deacetylase inhibitors

  摘要：

  In an effort to discover novel non-hydroxamic acid histone deacetylase (HDAC) inhibitors, a novel alpha-mercaptoketone was identified in a high-throughput screen. Lead optimization of the screening hit, led to a number of potent HDAC inhibitors. In particular, alpha-mercaptoketone 19y (KD5150) exhibited nanomolar in vitro activity and inhibition of tumor growth in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.058
• 作为产物：
  描述：

  4-氟苯磺酰氯 在 吡啶 、 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N-[4-(2-bromoacetyl)phenyl]-4-fluorobenzenesulfonamide
  参考文献：
  名称：

  Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators

  摘要：

  Pyruvate kinase M2 isoform (PKM2) is a crucial protein responsible for aerobic glycolysis of cancer cells. Activation of PKM2 may alter aberrant metabolism in cancer cells. In this study, we discovered a 4-hydroxy-thiazolidine-2-thione compound 2 as a novel PKM2 activator from a random screening of an in-house compound library. Then a series of novel 4-hydroxy-thiazolidine-2-thione derivatives were designed and synthesized for screening as potent PKM2 activators. Among these, some compounds showed higher PKM2 activation activity than lead compound 2 and also exhibited significant anti proliferative activities on human cancer cell lines at nanomolar concentration. The compound 5w was identified as the most potent antitumor agent, which showed excellent anti-proliferative effects with IC50 values from 0.46 mu M to 0.81 mu M against H1299, HCT116, Hela and PC3 cell lines. 5w also showed less cytotoxicity in non-tumor cell line HELF compared with cancer cells. In addition, Preliminary pharmacological studies revealed that 5w arrests the cell cycle at the G2/M phase in HCT116 cell line. The best PKM2 activation by compound 5t was rationalized through docking studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.023