2-amino-3-bromo-5-(3',4'-methylenedioxyphenyl)-1,4-pyrazine | 350819-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-amino-3-bromo-5-(3',4'-methylenedioxyphenyl)-1,4-pyrazine
• CAS: 350819-25-9
• 化学式: C₁₁H₈BrN₃O₂
• 分子量: 294.107
• InChiKey: QTXOERIEGWRALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.26
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-amino-3-bromo-5-(3',4'-methylenedioxyphenyl)-1,4-pyrazine 在 盐酸 、 二(氰基苯)二氯化钯 、 aluminum tri-bromide 、 sodium carbonate 、 1,4-双(二苯基膦)丁烷 、 乙硫醇 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 46.0h， 生成 2-methyl-6-(3',4'-dihydroxyphenyl)-8-(4'-hydroxyphenyl)-3,7-dihydroimidazolo[1,2-a]pyrazin-3-one dihydrochloride
  参考文献：
  名称：

  Catechol derivatives of aminopyrazine and cell protection against uvb-induced mortality

  摘要：

  A series of 5-aryl- and 3,5-bis-aryl-7-amino- 1,4-pyrazine: derivatives 4 acid 6, and related imidazolopyrazinones 7, has been synthesized, the aryl groups of which are catechol and or phenol substituents. These compounds, tested against human keratinocyte cells stressed by UVB irradiation, showed high antioxidative properties. One compound (6f) was more active than EGCG; ECG (green tea extract) in reducing cell mortality. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00321-7
• 作为产物：
  描述：

  2-amino-5-(3',4'-methylenedioxyphenyl)-1,4-pyrazine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 以96%的产率得到2-amino-3-bromo-5-(3',4'-methylenedioxyphenyl)-1,4-pyrazine
  参考文献：
  名称：

  Catechol derivatives of aminopyrazine and cell protection against uvb-induced mortality

  摘要：

  A series of 5-aryl- and 3,5-bis-aryl-7-amino- 1,4-pyrazine: derivatives 4 acid 6, and related imidazolopyrazinones 7, has been synthesized, the aryl groups of which are catechol and or phenol substituents. These compounds, tested against human keratinocyte cells stressed by UVB irradiation, showed high antioxidative properties. One compound (6f) was more active than EGCG; ECG (green tea extract) in reducing cell mortality. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00321-7