2-amino-3-benzyl-5-ethynylpyrazine | 1268631-69-1

• 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-benzyl-5-ethynylpyrazine
• 英文别名: 3-benzyl-5-ethynylpyrazin-2-amine；3-Benzyl-5-ethynylpyrazin-2-amine
• CAS: 1268631-69-1
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: TUIODYDYMUDNND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-benzyl-5-ethynylpyrazine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 2-benzyl-8-benzyl-6-[1-(3-hydroxypropyl)-1,2,3-triazol-4-yl]imidazo[1,2-a]pyrazin-3(7H)-one
  参考文献：
  名称：

  Novel bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution for Renilla luciferase

  摘要：

  新型腔肠素类似物在细胞内展现出优异的生物发光特性，因此成为生物发光技术的理想分子。

  DOI：

  10.1039/c6ob00659k
• 作为产物：
  描述：

  5-amino-6-benzyl-2-O-trifluoromethanesulfonyloxypyrazine 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-amino-3-benzyl-5-ethynylpyrazine
  参考文献：
  名称：

  Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

  摘要：

  Synthesis of coelenterazine analogs is in recent demand to supply more luminescent compounds with reasonable stability as substrate for the photoprotein manipulated in a living cells or particular organelle. There are limited methods for the synthesis of 6-substituted coelenterazine due to the route and instability of the compounds under the existing conditions. This paper describes six examples including Suzuki-Miyaura cross coupling reaction with reactive triflate (unstable) and stable tosylate intermediates of the imidazo[1,2-a]pyrazin-3-one. Five examples of 2-amino-3-benzyl-5-O-Tf-pyrazine are also discussed. The product coelenterazine analogs are obtained in the form of dehydrocoelenterazine, which is the substrate of a squid photoprotein, symplectin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.001

文献信息

• 一种腔肠素类似物及其制备方法与应用
  申请人：山东大学

  公开号：CN105968114B

  公开（公告）日：2018-11-09

  本发明公开了一种腔肠素类似物及其制备方法与应用，具有结构通式(I)，式中，R1，R2，R3均为不同的取代基。该类化合物作为生物发光底物的应用，能利用生物发光检测腔肠素萤光素酶的存在和数量(包括酶水平、细胞水平和动物水平)，检测萤光素酶在体外，细胞和体内分布成像的应用；能够在萤光素酶的存在下作为报告信号检测药物在酶水平、细胞水平、动物水平的药理作用和毒性作用。
• Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies
  作者：Wong Phakhodee、Mitsuko Toyoda、Chun-Ming Chou、Nisachon Khunnawutmanotham、Minoru Isobe

  DOI：10.1016/j.tet.2010.12.001

  日期：2011.2

  Synthesis of coelenterazine analogs is in recent demand to supply more luminescent compounds with reasonable stability as substrate for the photoprotein manipulated in a living cells or particular organelle. There are limited methods for the synthesis of 6-substituted coelenterazine due to the route and instability of the compounds under the existing conditions. This paper describes six examples including Suzuki-Miyaura cross coupling reaction with reactive triflate (unstable) and stable tosylate intermediates of the imidazo[1,2-a]pyrazin-3-one. Five examples of 2-amino-3-benzyl-5-O-Tf-pyrazine are also discussed. The product coelenterazine analogs are obtained in the form of dehydrocoelenterazine, which is the substrate of a squid photoprotein, symplectin. (C) 2010 Elsevier Ltd. All rights reserved.
• Novel bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution for Renilla luciferase
  作者：Tianyu Jiang、Xiaofeng Yang、Xingye Yang、Mingliang Yuan、Tianchao Zhang、Huateng Zhang、Minyong Li

  DOI：10.1039/c6ob00659k

  日期：——

  Novel coelenterazine analogues displayed excellent bioluminescence propertiesin cellulo, thus becoming favourable molecules for bioluminescence techniques.

  新型腔肠素类似物在细胞内展现出优异的生物发光特性，因此成为生物发光技术的理想分子。