[bis(3-bromophenyl)ketone]ethylthiosemicarbazone | 1220124-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [bis(3-bromophenyl)ketone]ethylthiosemicarbazone
• 英文别名: 2-(bis(3-bromophenyl)methylene)-N-ethylhydrazinecarbothioamide；1-[bis(3-bromophenyl)methylideneamino]-3-ethylthiourea
• CAS: 1220124-33-3
• 化学式: C₁₆H₁₅Br₂N₃S
• 分子量: 441.189
• InChiKey: CXQWYHDDYQTDBT-UHFFFAOYSA-N

物化性质

• 沸点：
  497.6±55.0 °C(predicted)
• 密度：
  1.57±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-乙基-3-硫代氨基脲 、 3,3'-二溴二苯甲酮 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以84%的产率得到[bis(3-bromophenyl)ketone]ethylthiosemicarbazone
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors

  摘要：

  A small library of 36 functionalized benzophenone thiosemicarbazone analogs has been prepared by chemical synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. Inhibitors of cathepsins L and B have the potential to limit or arrest cancer metastasis. The six most active inhibitors of cathepsin L (IC50 < 85 nM) in this series incorporate a meta-bromo sub-stituent in one aryl ring along with a variety of functional groups in the second aryl ring. These six analogs are selective for their inhibition of cathepsin L versus cathepsin B (IC50 > 10,000 nM). The most active analog in the series, 3-bromophenyl-2'-fluorophenyl thiosemicarbazone 1, also efficiently inhibits cell invasion of the DU-145 human prostate cancer cell line. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.090

文献信息

• Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors
  作者：G.D. Kishore Kumar、Gustavo E. Chavarria、Amanda K. Charlton-Sevcik、Wara M. Arispe、Matthew T. MacDonough、Tracy E. Strecker、Shen-En Chen、Bronwyn G. Siim、David J. Chaplin、Mary Lynn Trawick、Kevin G. Pinney

  DOI：10.1016/j.bmcl.2009.12.090

  日期：2010.2

  A small library of 36 functionalized benzophenone thiosemicarbazone analogs has been prepared by chemical synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. Inhibitors of cathepsins L and B have the potential to limit or arrest cancer metastasis. The six most active inhibitors of cathepsin L (IC50 < 85 nM) in this series incorporate a meta-bromo sub-stituent in one aryl ring along with a variety of functional groups in the second aryl ring. These six analogs are selective for their inhibition of cathepsin L versus cathepsin B (IC50 > 10,000 nM). The most active analog in the series, 3-bromophenyl-2'-fluorophenyl thiosemicarbazone 1, also efficiently inhibits cell invasion of the DU-145 human prostate cancer cell line. (C) 2010 Elsevier Ltd. All rights reserved.