6-[(2,5-dimethylanilino)methyl]-2-ethyl-3H-quinazolin-4-one | 1258879-25-2

• 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: 6-[(2,5-dimethylanilino)methyl]-2-ethyl-3H-quinazolin-4-one
• CAS: 1258879-25-2
• 化学式: C₁₉H₂₁N₃O
• 分子量: 307.395
• InChiKey: YLXAJPHQAJMKNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-ethyl-6-methyl-4H-benzo[d][1,3]oxazin-4-one 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 formamide 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 6-[(2,5-dimethylanilino)methyl]-2-ethyl-3H-quinazolin-4-one
  参考文献：
  名称：

  Fragment-Based Design of Novel Quinazolinon Derivatives as Human Acrosin Inhibitors

  摘要：

  Human acrosin is a promising target for the male contraceptives. On the basis of the active site of human acrosin, a series of novel quinazolinon compounds were designed by a fragment docking and growing strategy. In vitro anti‐acrosin assay revealed that all the compounds showed potent human acrosin inhibitory activities. In particular, compounds 5c and 5g are more active than the known inhibitors. Molecular docking studies revealed that the quinazolinon inhibitors interacted with human acrosin mainly through hydrogen bonding and hydrophobic interactions. The binding mode was also consistent with the structure–activity relationships. The quinazolinon derivatives in this study can serve as new lead structure for the development of novel male contraceptives.

  DOI：

  10.1111/cbdd.12106

文献信息

• Fragment-Based Design of Novel Quinazolinon Derivatives as Human Acrosin Inhibitors
  作者：Weiwei Ning、Ju Zhu、Canhui Zheng、Xuefei Liu、Yunlong Song、Youjun Zhou、Xiaomeng Zhang、Ling Zhang、Chunquan Sheng、Jiaguo Lv

  DOI：10.1111/cbdd.12106

  日期：2013.4

  Human acrosin is a promising target for the male contraceptives. On the basis of the active site of human acrosin, a series of novel quinazolinon compounds were designed by a fragment docking and growing strategy. In vitro anti‐acrosin assay revealed that all the compounds showed potent human acrosin inhibitory activities. In particular, compounds 5c and 5g are more active than the known inhibitors. Molecular docking studies revealed that the quinazolinon inhibitors interacted with human acrosin mainly through hydrogen bonding and hydrophobic interactions. The binding mode was also consistent with the structure–activity relationships. The quinazolinon derivatives in this study can serve as new lead structure for the development of novel male contraceptives.