5-[[5-bromo-2-[(2-bromophenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone | 893449-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[[5-bromo-2-[(2-bromophenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone
• 英文别名: 5-[[5-Bromo-2-[(2-bromophenyl)methoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one；5-[[5-bromo-2-[(2-bromophenyl)methoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 893449-38-2
• 化学式: C₁₇H₁₁Br₂NO₂S₂
• 分子量: 485.22
• InChiKey: HXNBAOLVPAWYLT-UHFFFAOYSA-N

物化性质

• 密度：
  1.85±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：>10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险类别：
  9
• 危险性防范说明：
  P501,P273,P260,P270,P264,P280,P391,P314,P337+P313,P305+P351+P338,P301+P312+P330
• 危险品运输编号：
  3077
• 危险性描述：
  H302,H319,H372,H410
• 包装等级：
  III

反应信息

• 作为产物：
  描述：

  罗丹宁 、 5-Bromo-2-[(2-bromophenyl)methoxy]benzaldehyde 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以100%的产率得到5-[[5-bromo-2-[(2-bromophenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone
  参考文献：
  名称：

  Rhodanine-based PRL-3 inhibitors blocked the migration and invasion of metastatic cancer cells

  摘要：

  PRL-3, phosphatase of regenerating liver-3, plays a role in cancer progression through its involvement in invasion, migration, metastasis, and angiogenesis. We synthesized rhodanine derivatives, CG-707 and BR-1, which inhibited PRL-3 enzymatic activity with IC50 values of 0.8 mu M and 1.1 mu M, respectively. CG-707 and BR-1 strongly inhibited the migration and invasion of PRL-3 overexpressing colon cancer cells without exhibiting cytotoxicity. The specificity of the inhibitors on PRL-3 phosphatase activity was confirmed by the phosphorylation recovery of known PRL-3 substrates such as ezrin and cytokeratin 8. The compounds selectively inhibited PRL-3 in comparison with other phosphatases, and CG-707 regulated epithelial-to-mesenchymal transition (EMT) marker proteins. The results of the present study reveal that rhodanine is a specific PRL-3 inhibitor and a good lead molecule for obtaining a selective PRL-3 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.092

文献信息

• Rhodanine-based PRL-3 inhibitors blocked the migration and invasion of metastatic cancer cells
  作者：Garam Min、Su-Kyung Lee、Hye-Nan Kim、Young-Min Han、Rhan-Hee Lee、Dae Gwin Jeong、Dong Cho Han、Byoung-Mog Kwon

  DOI：10.1016/j.bmcl.2013.04.092

  日期：2013.7

  PRL-3, phosphatase of regenerating liver-3, plays a role in cancer progression through its involvement in invasion, migration, metastasis, and angiogenesis. We synthesized rhodanine derivatives, CG-707 and BR-1, which inhibited PRL-3 enzymatic activity with IC50 values of 0.8 mu M and 1.1 mu M, respectively. CG-707 and BR-1 strongly inhibited the migration and invasion of PRL-3 overexpressing colon cancer cells without exhibiting cytotoxicity. The specificity of the inhibitors on PRL-3 phosphatase activity was confirmed by the phosphorylation recovery of known PRL-3 substrates such as ezrin and cytokeratin 8. The compounds selectively inhibited PRL-3 in comparison with other phosphatases, and CG-707 regulated epithelial-to-mesenchymal transition (EMT) marker proteins. The results of the present study reveal that rhodanine is a specific PRL-3 inhibitor and a good lead molecule for obtaining a selective PRL-3 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.