N-[3-benzyl-5-(4-methoxy-phenyl)-pyrazin-2-yl]-acetamide | 49842-01-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[3-benzyl-5-(4-methoxy-phenyl)-pyrazin-2-yl]-acetamide
• 英文别名: 2-acetylamino-3-benzyl-5-(4-methoxyphenyl)pyrazine；N-[3-benzyl-5-(4-methoxyphenyl)pyrazin-2-yl]acetamide
• CAS: 49842-01-5
• 化学式: C₂₀H₁₉N₃O₂
• 分子量: 333.39
• InChiKey: QPHQIXKQBDCTFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-benzyl-6-(4-methoxyphenyl)-2-methylimidazo[1,2-a]pyrazin-3(7H)-one 在 氧气 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 N-[3-benzyl-5-(4-methoxy-phenyl)-pyrazin-2-yl]-acetamide
  参考文献：
  名称：

  Substituent Effects on the Chemiluminescent Properties of Coelenterazine Analogues

  摘要：

  在二甲基亚砜中测量了在 6-苯基对位上具有取代基 R [=CF3, F, H, OCH3, OH, N(CH3)2] 的腔肠素类似物的化学发光最大值和量子产率。结果表明，这些类似物中 R 的电子特性的变化导致单色激发光源化学生成效率（Φs）的微小变化。

  DOI：

  10.1246/cl.1998.95

文献信息

• COELENTERAMIDE ANALOGS
  申请人：Hosoya Takamitsu

  公开号：US20110288280A1

  公开（公告）日：2011-11-24

  There has been a need for coelenteramide analogs or the like that produce fluorescent proteins which exhibit different fluorescent characteristics from those of the existing fluorescent proteins. Disclosed is a compound represented by general formula (1) (wherein R 1 represents a substituted or unsubstituted aryl, a substituted or unsubstituted arylalkyl, a straight or branched alkyl which may optionally be substituted with an alicyclic group, an alicyclic group or a heterocyclic group; R 2 represents hydrogen or —(SO 2 )R 4 ; R 3 represents hydrogen, hydroxyl, methoxy or acetoxy; R 4 represents a substituted or unsubstituted aryl, a substituted or unsubstituted arylalkyl or a straight or branched alkyl which may optionally be substituted with an alicyclic group; and X 1 represents —C(═S)— or —SO 2 —).

  已经有了对产生发出与现有荧光蛋白不同荧光特性的珊瑚胺类似物等的需求。公开了一种由通式（1）表示的化合物（其中R1代表取代或未取代芳基，取代或未取代芳基烷基，可选择性地取代有脂环基的直链或支链烷基，脂环基或杂环基；R2代表氢或—(SO2)R4；R3代表氢，羟基，甲氧基或乙酰氧基；R4代表取代或未取代芳基，取代或未取代芳基烷基或可选择性地取代有脂环基的直链或支链烷基；X1代表—C(═S)—或—SO2—）。
• Solvent and substituent effects on the fluorescent properties of coelenteramide analogues
  作者：Ryota Saito、Takashi Hirano、Haruki Niwa、Mamoru Ohashi

  DOI：10.1039/a701156c

  日期：——

  Coelenteramide 1 is the light emitter in aequorin bioluminescence. To establish the fluorescent character of 1, the fluorescence properties of 1 and a series of its analogues, 3a–f, possessing a substituent R [= CF3, F, H, OCH3, OH, N(CH3)2] at the para-position on the 5-phenyl group have been investigated in solvents of various polarity. The fluorescence emission maxima of 1 and 3d–f, possessing an electron-donating group R [= OCH3, OH, N(CH3)2] shift to lower energy with increasing solvent polarity, while those of the analogues 3a–c (R = CF3, F, H) are independent of the solvent polarity. The linear correlation between the fluorescence maxima of 1 and 3d–f and the solvent polarity scales can be explained by formation of the singlet excited state with a charge-transfer (CT) character. The quantum yields of CT fluorescence of 1 and 3d–f have been found to be higher than those of 3a–c. These results indicate that the solvatochromic fluorescence of 1 originates from the CT excited state and the existence of an electron donating hydroxy group on the 5-phenyl group is essential for determining a wavelength and a high fluorescence quantum yield of aequorin bioluminescence.

  腔肠素1是海萤素生物发光中的发光体。为了确定1的荧光特性，在各种极性的溶剂中研究了1及其一系列类似物3a-f的荧光特性，这些类似物在5-苯基基团的对位上具有取代基R（= CF3、F、H、OCH3、OH、N（CH3）2）。1和3d-f的荧光发射最大值具有电子供体基团R（= OCH3、OH、N（CH3）2），随着溶剂极性的增加，其最大值向较低能量移动，而类似物3a-c（R= CF3、F、H）的荧光发射最大值与溶剂极性无关。1和3d-f的荧光最大值与溶剂极性尺度之间的线性相关性可以用具有电荷转移（CT）特征的单线态激发态的形成来解释。1和3d-f的CT荧光量子产率高于3a-c。这些结果表明，1的溶剂致色荧光来自CT激发态，5-苯基基团上存在电子供体羟基对于确定海萤素生物发光的波长和高荧光量子产率至关重要。
• Coelenteramide analogs
  申请人：Hosoya Takamitsu

  公开号：US08431525B2

  公开（公告）日：2013-04-30

  There has been a need for coelenteramide analogs or the like that produce fluorescent proteins which exhibit different fluorescent characteristics from those of the existing fluorescent proteins. Disclosed is a compound represented by general formula (1) (wherein R1 represents a substituted or unsubstituted aryl, a substituted or unsubstituted arylalkyl, a straight or branched alkyl which may optionally be substituted with an alicyclic group, an alicyclic group or a heterocyclic group; R2 represents hydrogen or —(SO2)R4; R3 represents hydrogen, hydroxyl, methoxy or acetoxy; R4 represents a substituted or unsubstituted aryl, a substituted or unsubstituted arylalkyl or a straight or branched alkyl which may optionally be substituted with an alicyclic group; and X1 represents —C(═S)— or —SO2—).

  有需要制备与coelenteramide类似的化合物或其他化合物，这些化合物能够产生不同于现有荧光蛋白的荧光特性。本发明揭示了一种化合物，其通式为（1）（其中，R1代表取代或未取代的芳基，取代或未取代的芳基烷基，可选地用含脂环基的直链或支链烷基取代的直链或支链烷基，脂环基或杂环基；R2代表氢或—（SO2）R4；R3代表氢，羟基，甲氧基或乙酰氧基；R4代表取代或未取代的芳基，取代或未取代的芳基烷基或可选地用含脂环基的直链或支链烷基取代的直链或支链烷基；X1代表—C（═S）—或—SO2—）。
• FLUORESCENT PROTEIN
  申请人：Chisso Corporation

  公开号：EP1666488B1

  公开（公告）日：2010-11-17
• Fluorescent Proteins
  申请人：Inouye Satoshi

  公开号：US20110070656A1

  公开（公告）日：2011-03-24

  A fluorescent protein (bFP) having chemiluminescence activity is a complex composed of the apoprotein of a calcium-binding photoprotein, coelenteramid or an analog thereof, and calcium ions or divalent or trivalent ions that can be substituted for the calcium ions. In the complex, the ratio of the number of molecules of the apoprotein to that of the coelenteramid is 1:1 and the ratio of the number of molecules of the apoprotein to that of the divalent or trivalent ions is 1:1 to 1:4. The fluorescent protein is used as a marker because it catalyzes luminescence of coelenterazine and has fluorescence capability. Removal of calcium ions etc. from this fluorescent protein (bFP) having luminescence activity provides a novel fluorescent protein (gFP). Mixing this gFP with the coelenterazine provides a calcium-binding photoprotein, which emit light instantaneously, enabling use as a marker.