2-[5-(hydroxymethyl)thiophen-2-yl]-1-methyl-3-phenyl-2H-quinazolin-4-one | 1429192-46-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[5-(hydroxymethyl)thiophen-2-yl]-1-methyl-3-phenyl-2H-quinazolin-4-one
• CAS: 1429192-46-0
• 化学式: C₂₀H₁₈N₂O₂S
• 分子量: 350.441
• InChiKey: PXQKOVNESNVWQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[5-(hydroxymethyl)thiophen-2-yl]-1-methyl-3-phenyl-2H-quinazolin-4-one 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以33%的产率得到2-[5-(chloromethyl)thiophen-2-yl]-1-methyl-3-phenyl-2H-quinazolin-4-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：

  5-(1-methyl-4-oxo-3-phenyl-2H-quinazolin-2-yl)thiophene-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 以100%的产率得到2-[5-(hydroxymethyl)thiophen-2-yl]-1-methyl-3-phenyl-2H-quinazolin-4-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