5-(4-(2-oxo-2-phenylethoxy)benzylidene)-1,3-bis(2-oxo-2-phenylethyl)imidazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-(2-oxo-2-phenylethoxy)benzylidene)-1,3-bis(2-oxo-2-phenylethyl)imidazolidine-2,4-dione
• 英文别名: 1,3-diphenacyl-5-[(4-phenacyloxyphenyl)methylidene]imidazolidine-2,4-dione
• 化学式: C₃₄H₂₆N₂O₆
• 分子量: 558.59
• InChiKey: JHHXIJKFDSUQPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 在 哌啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 5-(4-(2-oxo-2-phenylethoxy)benzylidene)-1,3-bis(2-oxo-2-phenylethyl)imidazolidine-2,4-dione 、 5-(4-(2-oxo-2-phenylethoxy)benzylidene)imidazolidine-2,4-dione
  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

文献信息

• Synthesis, biological evaluation and 3D-QSAR studies of imidazolidine-2,4-dione derivatives as novel protein tyrosine phosphatase 1B inhibitors
  作者：Mei-Yan Wang、Yuan-Yuan Jin、Hui-Yu Wei、Li-Song Zhang、Su-Xia Sun、Xiu-Bo Chen、Wei-Li Dong、Wei-Ren Xu、Xian-Chao Cheng、Run-Ling Wang

  DOI：10.1016/j.ejmech.2015.08.037

  日期：2015.10

  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.