3-benzyl-6,7,8-trihydroxy-2-phenylquinazolin-4(3H)-one | 1488139-74-7

• 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: 3-benzyl-6,7,8-trihydroxy-2-phenylquinazolin-4(3H)-one
• 英文别名: 3-Benzyl-6,7,8-trihydroxy-2-phenylquinazolin-4-one；3-benzyl-6,7,8-trihydroxy-2-phenylquinazolin-4-one
• CAS: 1488139-74-7
• 化学式: C₂₁H₁₆N₂O₄
• 分子量: 360.369
• InChiKey: JQFLKAJQKGNCSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-硝基-3,4,5-三甲氧基苯甲酸甲酯 在 吡啶 、 盐酸 、 tin(II) chloride dihdyrate 、 ammonium acetate 、 水 、 三溴化硼 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-benzyl-6,7,8-trihydroxy-2-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  Design and application of a rigid quinazolone scaffold based on two-face Bim α-helix mimicking

  摘要：

  Based on our previous discovery of an anthraquinone scaffold mimicking two faces of Bim a-helix, we derived a quinazolone scaffold through structure simplification and optimization. It was inferred that a rigid bicyclic ring was necessary and efficient to maintain the two-faced binding mode. A novel dual inhibitor 6c [6,7,8-trihydroxy-3-(2-hydroxy-5-methylbenzyl)-2-phenylquinazolin-4(3H)-one] was obtained based on this scaffold. 6c exhibited dual binding activity with Ki values of 0.123 mu M for Mcl-1 and 0.179 mu M for Bcl-2. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.030

文献信息

• Design and application of a rigid quinazolone scaffold based on two-face Bim α-helix mimicking
  作者：Zhichao Zhang、Xiaomeng Liang、Xiangqian Li、Ting Song、Qingbin Chen、Hongkun Sheng

  DOI：10.1016/j.ejmech.2013.09.030

  日期：2013.11

  Based on our previous discovery of an anthraquinone scaffold mimicking two faces of Bim a-helix, we derived a quinazolone scaffold through structure simplification and optimization. It was inferred that a rigid bicyclic ring was necessary and efficient to maintain the two-faced binding mode. A novel dual inhibitor 6c [6,7,8-trihydroxy-3-(2-hydroxy-5-methylbenzyl)-2-phenylquinazolin-4(3H)-one] was obtained based on this scaffold. 6c exhibited dual binding activity with Ki values of 0.123 mu M for Mcl-1 and 0.179 mu M for Bcl-2. (C) 2013 Elsevier Masson SAS. All rights reserved.