(E)-methyl 4-((4-((3-benzyl-1-(2-methoxy-2-oxoethyl)-2,5-dioxoimidazolidin-4-ylidene)methyl)phenoxy)methyl)benzoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-methyl 4-((4-((3-benzyl-1-(2-methoxy-2-oxoethyl)-2,5-dioxoimidazolidin-4-ylidene)methyl)phenoxy)methyl)benzoate
• 英文别名: methyl 4-[[4-[(E)-[3-benzyl-1-(2-methoxy-2-oxoethyl)-2,5-dioxoimidazolidin-4-ylidene]methyl]phenoxy]methyl]benzoate
• 化学式: C₂₉H₂₆N₂O₇
• 分子量: 514.535
• InChiKey: BPTKHXBWFFILDQ-PCLIKHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-methyl 4-((4-((3-benzyl-1-(2-methoxy-2-oxoethyl)-2,5-dioxoimidazolidin-4-ylidene)methyl)phenoxy)methyl)benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以23.05%的产率得到(E)-4-((4-((3-benzyl-1-(carboxymethyl)-2,5-dioxoimidazolidin-4-ylidene)methyl)phenoxy)methyl)benzoic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and 3D-QSAR studies of imidazolidine-2,4-dione derivatives as novel protein tyrosine phosphatase 1B inhibitors

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) plays a vital role in the regulation of insulin sensitivity and dephosphorylation of the insulin receptor, so PTP1B inhibitors may be potential agents to treat type 2 diabetes. In this work, a series of novel imidazolidine-2,4-dione derivatives were designed, synthesized and assayed for their PTP1B inhibitory activities. These compounds exhibited potent activities with IC50 values at 0.57-172 mu M. A 3D-QSAR study using CoMFA and CoMSIA techniques was carried out to explore structure activity relationship of these molecules. The CoMSIA model was more predictive with q(2) = 0.777, r(2) = 0.999, SEE = 0.013 and r(pred)(2) = 0.836, while the CoMFA model gave q(2) = 0.543, r(2) = 0.998, SEE = 0.029 and r(pred)(2) = 0354. The contour maps derived from the best CoMFA and CoMSIA models combined with docking analysis provided good insights into the structural features relevant to the bioactivity, and could be used in the molecular design of novel imidazolidine-2,4-dione derivatives. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.037
• 作为产物：
  描述：

  1-苄基乙内酰脲 在 哌啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.5h， 生成 (E)-methyl 4-((4-((3-benzyl-1-(2-methoxy-2-oxoethyl)-2,5-dioxoimidazolidin-4-ylidene)methyl)phenoxy)methyl)benzoate
  参考文献：
  名称：

  Synthesis, biological evaluation and 3D-QSAR studies of imidazolidine-2,4-dione derivatives as novel protein tyrosine phosphatase 1B inhibitors

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) plays a vital role in the regulation of insulin sensitivity and dephosphorylation of the insulin receptor, so PTP1B inhibitors may be potential agents to treat type 2 diabetes. In this work, a series of novel imidazolidine-2,4-dione derivatives were designed, synthesized and assayed for their PTP1B inhibitory activities. These compounds exhibited potent activities with IC50 values at 0.57-172 mu M. A 3D-QSAR study using CoMFA and CoMSIA techniques was carried out to explore structure activity relationship of these molecules. The CoMSIA model was more predictive with q(2) = 0.777, r(2) = 0.999, SEE = 0.013 and r(pred)(2) = 0.836, while the CoMFA model gave q(2) = 0.543, r(2) = 0.998, SEE = 0.029 and r(pred)(2) = 0354. The contour maps derived from the best CoMFA and CoMSIA models combined with docking analysis provided good insights into the structural features relevant to the bioactivity, and could be used in the molecular design of novel imidazolidine-2,4-dione derivatives. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.037