3-[3-(2,3,5-Trimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoylamino]benzoic acid | 1426927-30-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-[3-(2,3,5-Trimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoylamino]benzoic acid
• 英文别名: 3-[3-(2,3,5-trimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoylamino]benzoic acid
• CAS: 1426927-30-1
• 化学式: C₂₄H₂₁NO₆
• 分子量: 419.434
• InChiKey: FYTBWSGXGAHVOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2',3',5'-trimethyl-7'-oxo-7H-furo[3,2-g][1]benzopyran-6'-yl)propionic acid 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 3-[3-(2,3,5-Trimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoylamino]benzoic acid
  参考文献：
  名称：

  Psoralen Derivatives as Inhibitors of NF-κB/DNA Interaction: Synthesis, Molecular Modeling, 3D-QSAR, and Biological Evaluation

  摘要：

  Some new psoralen derivatives were synthesized and evaluated as inhibitors of NF-kappa B/DNA interaction, with the aim to investigate the structural determinants required to inhibit this interaction. Starting from molecular docking studies, several possible protein binding sites were proposed and several three-dimensional quantitative structure activity relationship (3D-QSAR) models were built using the docked poses of 29 (the most active psoralen in the series) as templates for alignment of the inhibitors. The selected best model was validated through the prediction of the activity of 17 novel compounds. All the experimental data agreed with the computational experiments, supporting the reliability of the computational approach. The hypothesis about the interaction with NF-kappa B was also supported by surface plasmon resonance based assays using compound 29. All the collected data allowed the identification of compound 29 as a potential candidate for the development of pharmaceutical strategies against the inflammatory phenotype of cystic fibrosis.

  DOI：

  10.1021/jm3009647

文献信息

• Psoralen Derivatives as Inhibitors of NF-κB/DNA Interaction: Synthesis, Molecular Modeling, 3D-QSAR, and Biological Evaluation
  作者：Giovanni Marzaro、Adriano Guiotto、Monica Borgatti、Alessia Finotti、Roberto Gambari、Giulia Breveglieri、Adriana Chilin

  DOI：10.1021/jm3009647

  日期：2013.3.14

  Some new psoralen derivatives were synthesized and evaluated as inhibitors of NF-kappa B/DNA interaction, with the aim to investigate the structural determinants required to inhibit this interaction. Starting from molecular docking studies, several possible protein binding sites were proposed and several three-dimensional quantitative structure activity relationship (3D-QSAR) models were built using the docked poses of 29 (the most active psoralen in the series) as templates for alignment of the inhibitors. The selected best model was validated through the prediction of the activity of 17 novel compounds. All the experimental data agreed with the computational experiments, supporting the reliability of the computational approach. The hypothesis about the interaction with NF-kappa B was also supported by surface plasmon resonance based assays using compound 29. All the collected data allowed the identification of compound 29 as a potential candidate for the development of pharmaceutical strategies against the inflammatory phenotype of cystic fibrosis.