2-amino-3-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-1,4-pyrazine | 1178890-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-3-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-1,4-pyrazine
• 英文别名: 4-[5-Amino-6-(4-methoxyphenyl)pyrazin-2-yl]phenol；4-[5-amino-6-(4-methoxyphenyl)pyrazin-2-yl]phenol
• CAS: 1178890-02-2
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: PZOVBUAEODYNTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-3-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-1,4-pyrazine 、 丙酮醛 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以81%的产率得到2-methyl-6-(4-hydroxyphenyl)-8-(4-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one hydrochloride
  参考文献：
  名称：

  In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.05.025
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 以249 mg的产率得到2-amino-3-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-1,4-pyrazine
  参考文献：
  名称：

  In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.05.025

文献信息

• Chemical Synthesis of Coelenterazine and Its Analogs: New Route toward Four Segment-Couplings
  作者：Minoru Isobe、Chun-Ming Chou、Yu-Wen Tung、Meng-I Ling、Diana Chan、Wong Phakhodee

  DOI：10.3987/com-12-s(n)85

  日期：——

  A novel and improved synthetic route includes four segment-couplings toward coelenterazine and its analogs as luminescent molecules. Regio- and chemo-selective cross coupling reactions using palladium catalysts with 5-iodo-3-bromo-2-aminopyrazine have enabled providing various aminopyrazine derivatives having different substituents. The improved synthesis of coelenterazine and its analogs employed advanced condensation with the aminopyrazines using various keto-acetal segments, which resulted in much higher yields to give the final imidazopyrazinone heterocycles than the previous method using keto-aldehydes.