2-amino-3-bromo-5-(4'-methoxyphenyl)-1,4-pyrazine | 350819-24-8

• 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-bromo-5-(4'-methoxyphenyl)-1,4-pyrazine
• 英文别名: 2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine；2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine；3-bromo-5-(4-methoxyphenyl)pyrazin-2-amine
• CAS: 350819-24-8
• 化学式: C₁₁H₁₀BrN₃O
• 分子量: 280.124
• InChiKey: IWZUQUURKWFPAF-UHFFFAOYSA-N

物化性质

• 沸点：
  384.6±42.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-3-bromo-5-(4'-methoxyphenyl)-1,4-pyrazine 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以53%的产率得到4-(5-amino-6-bromopyrazin-2-yl)phenol
  参考文献：
  名称：

  Chemical Synthesis of Coelenterazine and Its Analogs: New Route toward Four Segment-Couplings

  摘要：

  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.

  DOI：

  10.3987/com-12-s(n)85
• 作为产物：
  描述：

  5-(4-甲氧基苯基)-2-氨基吡嗪 在 吡啶 、 溴 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以70%的产率得到2-amino-3-bromo-5-(4'-methoxyphenyl)-1,4-pyrazine
  参考文献：
  名称：

  [EN] IMIDAZO[1,2-a]PYRAZIN-3(7H)-ONE DERIVATIVES BEARING A NEW ELECTRON-RICH STRUCTURE
  [FR] DÉRIVÉS D'IMIDAZO[1,2-?]PYRAZIN-3(7H)-ONE PORTANT UNE NOUVELLE STRUCTURE RICHE EN ÉLECTRONS

  摘要：

  本发明涉及化合物I的公式：及其作为化学发光和/或生物发光试剂的用途。

  公开号：

  WO2011007314A1

文献信息

• IMIDAZO[1,2-ALPHA]PYRAZIN-3(7H)-ONE DERIVATIVES BEARING A NEW ELECTRON-RICH STRUCTURE
  申请人：Giuliani Germano

  公开号：US20120171703A1

  公开（公告）日：2012-07-05

  The present invention relates to compound of formula I: and their use as chemiluminescent and/or bioluminescent reagents.

  本发明涉及化合物I的配方和它们作为化学发光和/或生物发光试剂的用途。
• Imidazo[1,2-α]pyrazin-3(7H)-one derivatives bearing a new electron-rich structure
  申请人：Giuliani Germano

  公开号：US08546147B2

  公开（公告）日：2013-10-01

  The present invention relates to compound of formula I: and their use as chemiluminescent and/or bioluminescent reagents.

  本发明涉及式I的化合物，并将其用作化学发光和/或生物发光试剂。
• 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。
• New red-shifted coelenterazine analogues with an extended electronic conjugation
  作者：Germano Giuliani、Paola Molinari、Giulia Ferretti、Andrea Cappelli、Maurizio Anzini、Salvatore Vomero、Tommaso Costa

  DOI：10.1016/j.tetlet.2012.07.041

  日期：2012.9

  A new promising approach to the development of red-shifted coelenterazine analogues was described. In order to alter the photochemical properties of native coelenterazine, we have designed and synthesized analogues bearing a new electron-rich structure. The spectroscopic results obtained, in the presence of the target enzyme (Renilla Luciferase), show a bathochromic emission shift of the entire class of new derivatives. Among them, the 2-benzyl-8-(4-chlorophenylthio)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one (8) shows an emission at 510 nm and uncommon slow kinetic decay. (C) 2012 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.