6-((benzyl(methyl)amino)methyl)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-((benzyl(methyl)amino)methyl)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
• 英文别名: 6-((Benzyl(methyl)amino)methyl)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one (3c)；6-[[benzyl(methyl)amino]methyl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
• 化学式: C₂₄H₂₁NO₇
• 分子量: 435.433
• InChiKey: ILZHAKHRQTZBQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  131
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 槲皮素 、 N-甲基苄胺 以 异丙醇 为溶剂， 反应 5.0h， 以15%的产率得到6-((benzyl(methyl)amino)methyl)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and Molecular Docking of Novel Benzopyran and Phenylpyrazole Derivatives as Akt Inhibitors

  摘要：

  By inspiration of good Akt1 inhibitory and cytotoxic activity of our previously screened hits 1 and 2, a series of novel benzopyrans 3a–c, 4 and phenylpyrazoles 5a–c, 6a–b, and 7 were designed, synthesized, and biologically evaluated for their in vitro Akt1 inhibitory and cytotoxic activity. The results revealed that all of these compounds showed moderate‐to‐excellent antiproliferative effects against the tested cancer cell lines (i.e. HL‐60, OVCAR, PC‐3, and HepG2). Among them, compounds 3a and 3c exhibited preferable Akt1 inhibitory activities (IC50 of 3a and 3c are 6.18 and 5.28 μm, respectively), while compounds 4, 5a–c, 6a–b, and 7 only showed weak Akt1 inhibitory activities. Consequently, we used molecular docking and dynamic simulation to propose a mode of binding between Akt1 and the 3c compound.

  DOI：

  10.1111/cbdd.12489

文献信息

• Design, Synthesis, Biological Evaluation, and Molecular Docking of Novel Benzopyran and Phenylpyrazole Derivatives as Akt Inhibitors
  作者：Wenhu Zhan、Sendong Lin、Jing Chen、Xiaowu Dong、Jianbo Chu、Wenting Du

  DOI：10.1111/cbdd.12489

  日期：2015.6

  By inspiration of good Akt1 inhibitory and cytotoxic activity of our previously screened hits 1 and 2, a series of novel benzopyrans 3a–c, 4 and phenylpyrazoles 5a–c, 6a–b, and 7 were designed, synthesized, and biologically evaluated for their in vitro Akt1 inhibitory and cytotoxic activity. The results revealed that all of these compounds showed moderate‐to‐excellent antiproliferative effects against the tested cancer cell lines (i.e. HL‐60, OVCAR, PC‐3, and HepG2). Among them, compounds 3a and 3c exhibited preferable Akt1 inhibitory activities (IC50 of 3a and 3c are 6.18 and 5.28 μm, respectively), while compounds 4, 5a–c, 6a–b, and 7 only showed weak Akt1 inhibitory activities. Consequently, we used molecular docking and dynamic simulation to propose a mode of binding between Akt1 and the 3c compound.