5-(N-Boc-indol-3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 1357306-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(N-Boc-indol-3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: Tert-butyl 3-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]indole-1-carboxylate
• CAS: 1357306-42-3
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: NEZZTRQCAIDOMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(N-Boc-indol-3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 哌啶 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  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
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 3-甲酰基吲哚酸-1-羧酸 t-丁基酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 5-(N-Boc-indol-3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-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

文献信息

• 3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization
  作者：Kai Liu、Wei Rao、Hardik Parikh、Qianbin Li、Tai L. Guo、Steven Grant、Glen E. Kellogg、Shijun Zhang

  DOI：10.1016/j.ejmech.2011.10.031

  日期：2012.1

  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.