8-benzyl-2-(2,4-difluorobenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one | 1326236-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 英文名称: 8-benzyl-2-(2,4-difluorobenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one
• 英文别名: 8-benzyl-2-(2,4-difluorobenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazine-3(7H)-one；8-benzyl-2-[(2,4-difluorophenyl)methyl]-6-(4-hydroxyphenyl)-7H-imidazo[1,2-a]pyrazin-3-one
• CAS: 1326236-33-2
• 化学式: C₂₆H₁₉F₂N₃O₂
• 分子量: 443.453
• InChiKey: OVEZTEKDKQHZJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.91
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-benzyl-2-(2,4-difluorobenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one 在 manganese(IV) oxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 2.5h， 以64%的产率得到(Z)-8-benzyl-2-(2,4-difluorobenzylidene)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazine-3(2H)-one
  参考文献：
  名称：

  动态手性决定了Symplectin-Dehydrocoelenterazine系统中生物发光的关键作用。

  摘要：

  Symplectin是一种含有脱氢腔肠素（DCL）发色团的光蛋白，该发色团通过共价键与半胱氨酸残基连接在一起，发出蓝光。这项研究的重点是新兴的立体遗传学中心的立体化学过程。由于其不同的生物发光活性，使用了两种异构的氟化DCL类似物（2,4-diF-和2,6-diF-DCL），与天然DCL相比分别为200％和20％。发现这些diF-DCL中的每一个都可以在pH 6.0的辛普列汀中与天然DCL交换。新兴的立体异构碳在结合位点是外消旋的。将这种储存形式的pH值更改为蛋白质的最佳溶解度pH（pH 7.8），会导致2,4-diF-DCL结合的symplectin发光，然后对用过的溶液进行分析，并在肽酶消化后检测腔肠酰胺-390-CGLK-肽和腔肠胺。另一方面，对2,6-diF-DCL结合的symplectin的相同分析仅提供了腔肠素，而没有腔肠酰胺。当外消旋体diF‐DCL移至pH 7.8的活性位点

  DOI：

  10.1002/asia.201100089
• 作为产物：
  描述：

  在 盐酸 、 copper(II) oxide 、 copper dichloride 作用下， 以 甲醇 、 水 为溶剂， 反应 5.5h， 生成 8-benzyl-2-(2,4-difluorobenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one
  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

文献信息

• Molecular mechanism of Symplectoteuthis bioluminescence—Part 4: Chromophore exchange and oxidation of the cysteine residue
  作者：Chun-Ming Chou、Yu-Wen Tung、Minoru Isobe

  DOI：10.1016/j.bmc.2014.05.044

  日期：2014.8

  Symplectin is one of the few photoproteins, which forms covalent bonds with the dehydro-coelenterazine (DCL) at the binding sites and the active site. This binding takes place through the SH's of the cysteine residues via conjugate addition reaction. This photoprotein contains the chromophore molecules at the binding cites first, and then moves to the active cite Cys-390 for the luminescence. The current study focuses on these dynamic aspects of the chromophore using the natural photoprotein by analyzing the fluorescence changing of the DCL chromophores analogs with 8-(4'-methoxyphenyI)- or 8-(2'-naphthyl)-group and 2-(2',4'-difluorophenyl)-group. Exchanges of these chromophores were monitored the fluorescence at slightly acidic media and also from the luminescence function observed at the optimum pH 7.8. The non-fluorescent naphthyl analogs was even proven to make the covalent bond formation at pH 6.0 and evidently to obtain the corresponding luminescent product amide by liquid chromatographic detection from the spent solutions. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.
• Dynamic Chirality Determines Critical Roles for Bioluminescence in Symplectin-Dehydrocoelenterazine System
  作者：Vorawan Kongjinda、Yosuke Nakashima、Naoki Tani、Masaki Kuse、Toshio Nishikawa、Chin-Hui Yu、Nobuyuki Harada、Minoru Isobe

  DOI：10.1002/asia.201100089

  日期：2011.8.1

  diF‐DCLs moved to the active site at pH 7.8, a change in the chirality with the 390‐Cys residue resulted. Model experiments using L‐cysteine‐containing CGLK‐peptide supported two diastereoisomers from each diF‐DCL. The significant difference in the luminescence from these two chromophores is attributed to a plausible mechanism including the dynamically variable stereogenic center emerging at the storage and

  Symplectin是一种含有脱氢腔肠素（DCL）发色团的光蛋白，该发色团通过共价键与半胱氨酸残基连接在一起，发出蓝光。这项研究的重点是新兴的立体遗传学中心的立体化学过程。由于其不同的生物发光活性，使用了两种异构的氟化DCL类似物（2,4-diF-和2,6-diF-DCL），与天然DCL相比分别为200％和20％。发现这些diF-DCL中的每一个都可以在pH 6.0的辛普列汀中与天然DCL交换。新兴的立体异构碳在结合位点是外消旋的。将这种储存形式的pH值更改为蛋白质的最佳溶解度pH（pH 7.8），会导致2,4-diF-DCL结合的symplectin发光，然后对用过的溶液进行分析，并在肽酶消化后检测腔肠酰胺-390-CGLK-肽和腔肠胺。另一方面，对2,6-diF-DCL结合的symplectin的相同分析仅提供了腔肠素，而没有腔肠酰胺。当外消旋体diF‐DCL移至pH 7.8的活性位点