4,4-dimethyl-1H-quinazolin-2-amine | 1005550-38-8

• 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: 4,4-dimethyl-1H-quinazolin-2-amine
• CAS: 1005550-38-8
• 化学式: C₁₀H₁₃N₃
• 分子量: 175.233
• InChiKey: IDZLTPLBSAHGOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  溴化氰 、 2-(2-氨基-2-丙基)苯胺 反应 4.0h， 以97%的产率得到4,4-dimethyl-1H-quinazolin-2-amine
  参考文献：
  名称：

  Ligand Optimization by Improving Shape Complementarity at a Hepatitis C Virus RNA Target

  摘要：

  Crystal structure analysis revealed key interactions of a 2-amino-benzimidazole viral translation inhibitor that captures an elongated conformation of an RNA switch target in the internal ribosome entry site (IRES) of hepatitis C virus (HCV). Here, we have designed, and synthesized quinazoline derivatives with improved shape complementarity at the ligand binding site of the viral RNA target. A Spiro-cyclopropyl modification aimed at filling a pocket in the back of the RNA binding site led to a 5-fold increase of ligand affinity while a slightly more voluminous dimethyl substitution at the same position did not improve binding. We demonstrate that precise shape complementarity based solely on hydrophobic interactions contributes significantly to ligand binding even at a hydrophilic RNA target site such as the HCV IRES conformational switch.

  DOI：

  10.1021/acschembio.6b00687