3-(2-aminoethyl)-5-(3-(2-ethoxyphenyl)propylidene)thiazolidine-2,4-dione | 1309444-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-aminoethyl)-5-(3-(2-ethoxyphenyl)propylidene)thiazolidine-2,4-dione
• 英文别名: 3-(2-Aminoethyl)-5-[3-(2-ethoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione；3-(2-aminoethyl)-5-[3-(2-ethoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1309444-68-5
• 化学式: C₁₆H₂₀N₂O₃S
• 分子量: 320.412
• InChiKey: LDNVBMKHPICNBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙氧基苯甲醛 在 哌啶 、 盐酸 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 3-(2-aminoethyl)-5-(3-(2-ethoxyphenyl)propylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization

  摘要：

  A series of 2,5-disubstituted-thiazolidine-2,4-dione analogs based on the newly identified lead 1, a potential anticancer agent via the inhibition of the Raf/MEK/extracellular signal regulated kinase (ERK) and phosphatidylinositol 3-kinase (PI3K)/Akt signaling cascades, were synthesized and biologically characterized. A new lead structure, 15, was identified to have improved anti-proliferative activities in U937 cells, to induce apoptosis in U937, M12 and DU145 cancer cells, and to arrest U937 cells at the S-phase. Furthermore, Western blot analysis demonstrated a correlation of the anti-proliferative activity and blockade of the Raf/MEK/ERK and PI3K/Akt signaling pathways. Collectively, these results strongly encourage further optimization of 15 as a new lead with multi-target properties to develop more potent compounds as anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.031