2-[(3-methylthiophen-2-yl)methylideneamino]-N-phenylbenzamide | 904021-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(3-methylthiophen-2-yl)methylideneamino]-N-phenylbenzamide
• CAS: 904021-66-5
• 化学式: C₁₉H₁₆N₂OS
• 分子量: 320.415
• InChiKey: AYZVNSPNFTWMFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3-methylthiophen-2-yl)methylideneamino]-N-phenylbenzamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以272 mg的产率得到2-(3-methylthiophen-2-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  N-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin

  摘要：

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.

  DOI：

  10.1021/jm4002346
• 作为产物：
  描述：

  3-甲基噻吩醛 、 2’-氨基苯甲酰苯胺 以 甲醇 为溶剂， 生成 2-[(3-methylthiophen-2-yl)methylideneamino]-N-phenylbenzamide
  参考文献：
  名称：

  N-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin

  摘要：

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.

  DOI：

  10.1021/jm4002346

文献信息

• <i>N</i>-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin
  作者：Romain Noel、Neetu Gupta、Valérie Pons、Amélie Goudet、Maria Daniela Garcia-Castillo、Aurélien Michau、Jennifer Martinez、David-Alexandre Buisson、Ludger Johannes、Daniel Gillet、Julien Barbier、Jean-Christophe Cintrat

  DOI：10.1021/jm4002346

  日期：2013.4.25

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.