4-[2-(5-Methylthiophen-2-yl)-4-oxo-1,2-dihydroquinazolin-3-yl]benzonitrile | 1429192-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[2-(5-Methylthiophen-2-yl)-4-oxo-1,2-dihydroquinazolin-3-yl]benzonitrile
• 英文别名: 4-[2-(5-methylthiophen-2-yl)-4-oxo-1,2-dihydroquinazolin-3-yl]benzonitrile
• CAS: 1429192-20-0
• 化学式: C₂₀H₁₅N₃OS
• 分子量: 345.425
• InChiKey: ITHMBCYNXBVWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-cyanophenyl)-2-[(5-methylthiophen-2-yl)methylideneamino]benzamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-[2-(5-Methylthiophen-2-yl)-4-oxo-1,2-dihydroquinazolin-3-yl]benzonitrile
  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.