5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-8-[(4-methylpiperazin-1-yl)methyl]chromen-4-one | 1403667-25-3

• 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: 5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-8-[(4-methylpiperazin-1-yl)methyl]chromen-4-one
• 英文别名: 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-8-[(4-methylpiperazin-1-yl)methyl]chromen-4-one
• CAS: 1403667-25-3
• 化学式: C₂₁H₂₂N₂O₆
• 分子量: 398.415
• InChiKey: UOFUGLTYJUVSGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  红盏花素 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 60.5h， 生成 5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-8-[(4-methylpiperazin-1-yl)methyl]chromen-4-one
  参考文献：
  名称：

  Mannich bases of scutellarein as thrombin-inhibitors: Design, synthesis, biological activity and solubility

  摘要：

  Two series of 8-aminomethylated derivatives were prepared by Mannich reaction of scutellarein (2) with appropriate aliphatic amines, alicyclic amines and formaldehyde. All the compounds were tested for their thrombin inhibition activity through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH) assay using 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide (MTT) assay method and the solubility were assessed by ultraviolet (UV). The results showed that morpholinyl aminomethylene substituent derivative (3d) demonstrated stronger anticoagulant activity, better water solubility and good antioxidant activity compared with scutellarein (2), which warrants further development as a agent for ischemic cerebrovascular disease treatment. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.015

文献信息

• Mannich bases of scutellarein as thrombin-inhibitors: Design, synthesis, biological activity and solubility
  作者：Nian-Guang Li、Shu-Lin Song、Min-Zhe Shen、Yu-Ping Tang、Zhi-Hao Shi、Hao Tang、Qian-Ping Shi、Yi-Fan Fu、Jian-Ao Duan

  DOI：10.1016/j.bmc.2012.10.015

  日期：2012.12

  Two series of 8-aminomethylated derivatives were prepared by Mannich reaction of scutellarein (2) with appropriate aliphatic amines, alicyclic amines and formaldehyde. All the compounds were tested for their thrombin inhibition activity through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH) assay using 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide (MTT) assay method and the solubility were assessed by ultraviolet (UV). The results showed that morpholinyl aminomethylene substituent derivative (3d) demonstrated stronger anticoagulant activity, better water solubility and good antioxidant activity compared with scutellarein (2), which warrants further development as a agent for ischemic cerebrovascular disease treatment. (C) 2012 Elsevier Ltd. All rights reserved.