5-[3-[2-[(2-methylphenyl)methoxy]phenyl]prop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-4-one | 1443442-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[3-[2-[(2-methylphenyl)methoxy]phenyl]prop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1443442-58-7
• 化学式: C₂₀H₁₇NO₂S₂
• 分子量: 367.492
• InChiKey: QAJHSXRVGRPJFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  罗丹宁 、 3-[2-[(2-Methylphenyl)methoxy]phenyl]prop-2-enal 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以100%的产率得到5-[3-[2-[(2-methylphenyl)methoxy]phenyl]prop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
  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.