2-Amino-3,5-bis(p-hydroxyphenyl)-1,4-pyrazine | 350230-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-Amino-3,5-bis(p-hydroxyphenyl)-1,4-pyrazine
• 英文别名: 4-[5-Amino-6-(4-hydroxyphenyl)pyrazin-2-yl]phenol；4-[5-amino-6-(4-hydroxyphenyl)pyrazin-2-yl]phenol
• CAS: 350230-62-5
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: GVOBQMZAUBVHSN-UHFFFAOYSA-N

物化性质

• 沸点：
  489.3±40.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Amino-3,5-bis(p-hydroxyphenyl)-1,4-pyrazine 、 丙酮醛 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以67%的产率得到2-Methyl-6,8-bis(p-hydroxyphenyl)-3,7-dihydroimidazolo[1,2-a]pyrazin-3-one hydrochloride
  参考文献：
  名称：

  2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

  摘要：

  芳基硼酸与2,6-二胺-3,5-二溴-1,4-吡嗪（6）的耦合反应生成了2,6-二氨基-3,5-二芳基-1,4-吡嗪（7）。7与甲基乙二醛在水相乙醇-盐酸中反应，得到了N,N"-二取代产物8，而不是预期的 bicyclic 噁唑吡嗪酮1。2,6-二[1-(乙氧基羧基)-乙基氨基]-3,5-二芳基-1,4-吡嗪8是强效的AAPH诱导亚油酸过氧化的抑制剂。

  DOI：

  10.1055/s-2001-12764
• 作为产物：
  描述：

  3,5-双(4-甲氧基苯基)吡嗪-2-胺 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到2-Amino-3,5-bis(p-hydroxyphenyl)-1,4-pyrazine
  参考文献：
  名称：

  2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

  摘要：

  芳基硼酸与2,6-二胺-3,5-二溴-1,4-吡嗪（6）的耦合反应生成了2,6-二氨基-3,5-二芳基-1,4-吡嗪（7）。7与甲基乙二醛在水相乙醇-盐酸中反应，得到了N,N"-二取代产物8，而不是预期的 bicyclic 噁唑吡嗪酮1。2,6-二[1-(乙氧基羧基)-乙基氨基]-3,5-二芳基-1,4-吡嗪8是强效的AAPH诱导亚油酸过氧化的抑制剂。

  DOI：

  10.1055/s-2001-12764

文献信息

• Aryl-substituted n, n-heterocyclic compounds, method for their preparationand their use in therapeutics and diagnostics
  申请人：——

  公开号：US20040034225A1

  公开（公告）日：2004-02-19

  The present invention relates to an aryl substituted pyrazine compound of the general formula I, II, III or IV with the exception of a) 2-amino-3,5-bis(p-methoxyphenyl)-1,4-pyrazine (CD29), 2-amino-5-phenyl-1,4-pyrazine (CD12), 2-amino-5-(4-methoxyphenyl)-1,4-pyrazine (CD17) and 2-amino-5-(4-hydroxyphenyl)-1,4-pyrazine (CD22) and of b) their corresponding imidazolopyrazinone compounds. Another aspect of the invention relates to anti-oxidant compounds of formula V. Another aspect of the invention is a compound which upon oxidation results via a cascade in a second anti-oxidant compound and a third compound.

  本发明涉及通式 I、II、III 或 IV 的芳基取代的吡嗪化合物，但 a) 2-氨基-3,5-双(对甲氧基苯基)-1,4-吡嗪(CD29)除外、2-氨基-5-苯基-1,4-吡嗪(CD12)、2-氨基-5-(4-甲氧基苯基)-1,4-吡嗪(CD17)和 2-氨基-5-(4-羟基苯基)-1,4-吡嗪(CD22)，以及 b) 它们相应的咪唑吡嗪酮化合物。本发明的另一个方面涉及式 V 的抗氧化化合物。本发明的另一个方面是一种化合物，该化合物在氧化时通过级联反应生成第二种抗氧化化合物和第三种化合物。
• In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants
  作者：Frederic De Wael、Paul Jeanjot、Cédric Moens、Tony Verbeuren、Alex Cordi、Eliete Bouskela、Jean-François Rees、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmc.2009.05.025

  日期：2009.7

  A series of 5-aryl and 3,5-diaryl-2-amino-1,4-pyrazines and the derived imidazopyrazinones has been synthesized to study the chemical oxidative degradation of the bicyclic systems in vitro. Imidazopyrazinones mainly degraded following two independent pathways producing their precursors, namely aminopyrazines, and the corresponding amidopyrazines, respectively. Despite the fact that there is no influence of the substituent of the 3-aryl group on the ratio of the products aminopyrazine/amidopyrazine, diarylimidazopyrazinones and diarylaminopyrazines are good antioxidants in vivo. They protected against microvascular damages in ischemia/reperfusion with similar efficiencies. (C) 2009 Elsevier Ltd. All rights reserved.
• Catechol derivatives of aminopyrazine and cell protection against uvb-induced mortality
  作者：Jean-François Cavalier、Maggi Burton、Frédérique Dussart、Cécile Marchand、Jean-François Rees、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0968-0896(00)00321-7

  日期：2001.4

  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.
• PYRAZINE AND IMIDAZOPYRAZINE DERIVATIVES AS ANTIOXIDANTS
  申请人：UNIVERSITE CATHOLIQUE DE LOUVAIN

  公开号：EP1292580A1

  公开（公告）日：2003-03-19
• [EN] ARYL-SUBSTITUTED N,N-HETEROCYCLIC COMPOUNDS, METHOD FOR THEIR PREPARATION AND THEIR USE IN THERAPEUTICS AND DIAGNOSTICS<br/>[FR] DERIVES DE PYRAZINE ET D'IMIDAZOPYRAZINE COMME ANTIOXYDANTS
  申请人：UNIV LOUVAIN

  公开号：WO2001087853A1

  公开（公告）日：2001-11-22

  The present invention relates to an aryl substituted pyrazine compound of the general formula I, II, III or IV with the exception of a) 2-amino-3,5-bis(p-methoxyphenyl)-1,4-pyrazine (CD29), 2-amino-5-phenyl-1,4-pyrazine (CD12), 2-amino-5-(4-methoxyphenyl)-1,4-pyrazine (CD17) and 2-amino-5-(4-hydroxyphenyl)-1,4-pyrazine (CD22) and of b) their corresponding imidazolopyrazinone compounds.Another aspect of the invention relates to anti-oxidant compounds of formula V.Another aspect of the invention is a compound which upon oxidation results via a cascade in a second anti-oxidant compound and a third compound.