5-(4-hydroxyphenyl)-2-aminopyrazine | 204770-67-2

• 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: 5-(4-hydroxyphenyl)-2-aminopyrazine
• 英文别名: 2-amino-5-(4'-hydroxyphenyl)-1,4-pyrazine；2-amino-5-(p-hydroxyphenyl)-1,4-pyrazine；2-amino-5-(4-hydroxyphenyl)pyrazine；2-Amino-5-(4-hydroxyphenyl)pyrazine；4-(5-aminopyrazin-2-yl)phenol
• CAS: 204770-67-2
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: YOXDGVOTULWSDO-UHFFFAOYSA-N

物化性质

• 沸点：
  391.2±37.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-hydroxyphenyl)-2-aminopyrazine 在 吡啶 、 sodium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 21.5h， 生成 4-[4-(5-Acetylamino-pyrazin-2-yl)-phenoxy]-butyric acid
  参考文献：
  名称：

  新型环麦芽低聚糖（环糊精）结合的6-苯基咪唑并[1,2-a]吡嗪-3（7H）-one的合成及增强化学发光

  摘要：

  为了提供在水溶液中具有高发光效率的化学发光底物，研究了6-苯基咪唑并[1,2-a]吡嗪-3（7H）-one化合物在共价键合下的结构设计。产生生色团的环麦芽寡糖（环糊精）。环糊精结合的6-苯基咪唑并[1,2-a]吡嗪-3（7H）-一种化合物的合成是通过在6-苯基咪唑并[1,2-a]吡嗪-3（之间）形成酰胺键来实现的。 7H）-一和单-6-氨基-6-脱氧环糊精。研究了合成的环糊精结合的发光发色团的氧诱导化学发光性质。在pH 8.3磷酸盐缓冲液中的发光效率明显取决于结合的环糊精的种类以及生色团与环糊精之间的结合位点。环麦芽糖（β-环糊精）已共价连接到咪唑并[1,2-a]吡嗪-3（7H）-一个环系统的2位上的与环糊精结合的化合物的发光效率显示出与非环糊精发色团相比，最多可增强11倍，而与环麦芽六糖（α-环糊精）的连接不会导致增强。而且，该研究表明，涉及将发光的生色团共价结合到环糊精上以增强化学发光

  DOI：

  10.1016/s0008-6215(97)10059-3
• 作为产物：
  描述：

  5-(4-甲氧基苯基)-2-氨基吡嗪 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80%的产率得到5-(4-hydroxyphenyl)-2-aminopyrazine
  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

文献信息

• Novel spiro compounds
  申请人：——

  公开号：US20020188124A1

  公开（公告）日：2002-12-12

  Compounds of the general formula (I): 1 wherein Ar 1 represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V, and W each independently represent nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or hydroxy substituted methine; Y represents an optionally substituted imino or oxygen atom are described and claimed. These novel spiro compounds are useful as neuropeptide Y receptor antagonists and as agents for the treatment of various kinds of cardiovascular disorders, central nervous system disorders, metabolic diseases and the like.

  通式(I)的化合物： 1 其中Ar 1 代表可选地取代的芳基或杂芳基； n代表0或1； T、U、V和W各自独立地代表氮原子或可选地取代的次甲基基团，其中至少有两个代表所述次甲基基团； X代表次甲基或羟基取代的次甲基； Y代表可选地取代的亚氨基或氧原子被描述和声称。这些新型的螺环化合物作为神经肽Y受体拮抗剂以及用于治疗各种心血管疾病、中枢神经系统疾病、代谢性疾病等的药物是有用的。
• Spiro compounds
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US06335345B1

  公开（公告）日：2002-01-01

  Spiro compounds of the general formula (I): wherein Ar1 represents an optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V and W each represent a nitrogen atom or an optionally substituted methine group, wherein at least two of which represent said methine group; X represents methine; Y represents an optionally substituted imino or oxygen atom. These novel spiro compounds exhibit neuropeptide Y receptor (NPY) antagonistic activities and are useful as agents for the treatment of various diseases related to NPY, for example, cardiovascular disorders, central nervous system disorders, metobolic diseases and the like.

  通式（I）的螺环化合物：其中Ar1代表可选择取代的芳基或杂环芳基；n代表0或1；T、U、V和W分别代表氮原子或可选择取代的甲基基团，其中至少两个代表所述的甲基基团；X代表甲基；Y代表可选择取代的亚胺基或氧原子。这些新型螺环化合物表现出神经肽Y受体（NPY）拮抗活性，并可用作治疗与NPY相关的各种疾病的药物，例如心血管疾病、中枢神经系统疾病、代谢性疾病等。
• NOVEL SPIRO COMPOUNDS
  申请人：——

  公开号：US20020052371A1

  公开（公告）日：2002-05-02

  Compounds of the general formula (I): 1 (wherein Ar 1 represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V and W represent independently nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or nitrogen; Y represents optionally substituted imino or oxygen atom) exhibit NPY antagonistic activities and are useful as agents for the treatment of various diseases related to NPY, for example, cardiovascular disorders such as hypertension, nephropathy, heart disease, vasospasm, arteriosclerosis and the like, central nervous system disorders such as bulimia, depression, anxiety, seizure, epilepsy, dementia, pain, alcoholism, drug withdrawal and the like, metabolic diseases such as obesity, diabetes, hormone abnormality, hypercholesterolemia, hyperlipidemia and the like, sexual and reproductive dysfunction, gastro-intestinal disorder, respiratory disorder, inflammation or glaucoma, and the like.

  通式（I）化合物（其中Ar1代表可选取代的芳基或杂环芳基；n代表0或1；T、U、V和W独立地代表氮原子或可选取代的甲基基团，其中至少有两个代表所述甲基基团；X代表甲基或氮原子；Y代表可选取代的亚胺基或氧原子）表现出NPY拮抗活性，并且可用作治疗与NPY相关的各种疾病的药剂，例如心血管疾病，如高血压、肾病、心脏病、血管痉挛、动脉硬化等，中枢神经系统疾病，如暴食症、抑郁症、焦虑症、癫痫、痴呆、疼痛、酗酒、戒断等，代谢性疾病，如肥胖症、糖尿病、激素异常、高胆固醇血症、高脂血症等，性和生殖功能障碍、胃肠道疾病、呼吸系统疾病、炎症或青光眼等。
• 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.