2-bromo-N-methylsecoboldine | 1350562-41-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,6a-仲卟啉
• 英文名称: 2-bromo-N-methylsecoboldine
• 英文别名: 2-Bromo-N-methylsecoboldine；7-bromo-8-[2-(dimethylamino)ethyl]-3,5-dimethoxyphenanthrene-2,6-diol
• CAS: 1350562-41-2
• 化学式: C₂₀H₂₂BrNO₄
• 分子量: 420.303
• InChiKey: DJMGFTGWQJZQEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-N-methylsecoboldine 、 碘甲烷 以29%的产率得到2-bromo-N,N-dimethylsecoboldine iodide
  参考文献：
  名称：

  Synthesis and reactive oxygen species scavenging activity of halogenated alkaloids from boldine

  摘要：

  Six halogenated alkaloids have been semi-synthesized from natural boldine as starting material. Their antioxidant activity toward reactive oxygen species (ROS) generation by neutrophils stimulated with N-formyl-methionyl-leucyl-phenylalanine and in the hypoxanthine-xanthine oxidase system was evaluated. Most of the alkaloids synthesized inhibited ROS generation in both systems in a concentration-dependent manner. The alkaloids with phenolic substituents displayed more powerful anti-oxidative activity than those containing methoxylated groups. None of the alkaloids assayed had any effect on xanthine oxidase activity. Therefore, halogenated phenanthrene alkaloids can become in promising candidates for the development of novel and potent anti-inflammatory drugs.

  DOI：

  10.1007/s00044-011-9844-5
• 作为产物：
  描述：

  波尔定碱 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 作用下， 以 甲醇 、 乙醇 、 乙腈 、 三氟乙酸 为溶剂， 反应 51.0h， 生成 2-bromo-N-methylsecoboldine
  参考文献：
  名称：

  Synthesis and reactive oxygen species scavenging activity of halogenated alkaloids from boldine

  摘要：

  Six halogenated alkaloids have been semi-synthesized from natural boldine as starting material. Their antioxidant activity toward reactive oxygen species (ROS) generation by neutrophils stimulated with N-formyl-methionyl-leucyl-phenylalanine and in the hypoxanthine-xanthine oxidase system was evaluated. Most of the alkaloids synthesized inhibited ROS generation in both systems in a concentration-dependent manner. The alkaloids with phenolic substituents displayed more powerful anti-oxidative activity than those containing methoxylated groups. None of the alkaloids assayed had any effect on xanthine oxidase activity. Therefore, halogenated phenanthrene alkaloids can become in promising candidates for the development of novel and potent anti-inflammatory drugs.

  DOI：

  10.1007/s00044-011-9844-5

文献信息

• Synthesis and reactive oxygen species scavenging activity of halogenated alkaloids from boldine
  作者：Lara Milián、Rafael Ballesteros、María Jesús Sanz、María Amparo Blázquez

  DOI：10.1007/s00044-011-9844-5

  日期：2012.10

  Six halogenated alkaloids have been semi-synthesized from natural boldine as starting material. Their antioxidant activity toward reactive oxygen species (ROS) generation by neutrophils stimulated with N-formyl-methionyl-leucyl-phenylalanine and in the hypoxanthine-xanthine oxidase system was evaluated. Most of the alkaloids synthesized inhibited ROS generation in both systems in a concentration-dependent manner. The alkaloids with phenolic substituents displayed more powerful anti-oxidative activity than those containing methoxylated groups. None of the alkaloids assayed had any effect on xanthine oxidase activity. Therefore, halogenated phenanthrene alkaloids can become in promising candidates for the development of novel and potent anti-inflammatory drugs.